WO2004112951A2 - Preparation of ruthenium-based olefin metathesis catalysts - Google Patents

Preparation of ruthenium-based olefin metathesis catalysts Download PDF

Info

Publication number
WO2004112951A2
WO2004112951A2 PCT/US2004/019712 US2004019712W WO2004112951A2 WO 2004112951 A2 WO2004112951 A2 WO 2004112951A2 US 2004019712 W US2004019712 W US 2004019712W WO 2004112951 A2 WO2004112951 A2 WO 2004112951A2
Authority
WO
WIPO (PCT)
Prior art keywords
rucl
mes
smes
trimethylphenyl
bis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2004/019712
Other languages
French (fr)
Other versions
WO2004112951A3 (en
Inventor
Steven P. Nolan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of New Orleans Research and Technology Foundation Inc
Original Assignee
University of New Orleans Research and Technology Foundation Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of New Orleans Research and Technology Foundation Inc filed Critical University of New Orleans Research and Technology Foundation Inc
Priority to EP04755714A priority Critical patent/EP1654060A4/en
Publication of WO2004112951A2 publication Critical patent/WO2004112951A2/en
Publication of WO2004112951A3 publication Critical patent/WO2004112951A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2269—Heterocyclic carbenes
    • B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54—Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium

Definitions

  • the present invention relates to olefin metathesis. More particularly, the present invention relates to synthesis of olefin metathesis catalysts.
  • complex 1 has been synthesized by reaction of RuCl 2 (PPh 3 ) with diazo compound according to eq. 1.
  • US Patent 6,369,265 Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in kumada coupling reactions:
  • US Patent 6,362,357 Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions;
  • the present invention includes a process for the preparation of ruthenium- based olefin metathesis catalysts.
  • the inventor has discovered that Ru-carbene complexes can be made from the Ru-indenylidene complex by cross metathesis. Other prior art routes are described above in the Background of the Invention.
  • the present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising making Ru-carbene complexes from a Ru-indenylidene complex by cross metathesis.
  • the process includes providing a Ru-indenylidene complex and an excess of an olefin.
  • the present invention includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising eq. 3 or a process similar to eq. 3, with one or more of the following variations: in place of CI one could use other halides, pseudohalides, alkoxides, aryloxides, anionic species etc.;
  • PCy 3 can be N-heterocyclcic carbene (NHC), and mixed NHC/PR 3 combinations; either of the PCy3 can be any 2-electron donor.
  • the present invention includes a synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts comprising a cross metathesis reaction between (L 1 )Ru(L 2 )(3-phenylindenylid-l-ene)Cl 2 (where Li and L 2 can be two- electron donors) and an olefin.
  • at least one of the following ruthenium olefin metathesis catalysts is preferably isolated:
  • PCy3 can be N-heterocyclcic carbene (NHC), and mixed NHC/PR combinations; in general either of the PCy can be any 2-electron donor.
  • complex 1 could be synthesized via a cross metathesis reaction according to eq. 3 eliminating the need for hazardous handling of a diazo reagent.
  • PCy3 can be N- heterocyclcic carbene (NHC), and mixed NHC/PR 3 combinations; in general either of the PCy 3 can be any 2-electron donor.
  • the present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, including those mentioned above in the Background of the Invention.
  • the inventor has discovered that Ru-carbene complexes can be made from the Ru-indenylidene complex by cross metathesis.
  • the present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising making Ru-carbene complexes from a Ru-indenylidene complex by cross metathesis.
  • the process includes providing a Ru-indenylidene complex and an excess of an olefin.
  • the present invention includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising eq. 3 or a process similar to eq. 3, with one or more of the following variations: in place of CI one could use other halides, pseudohalides, aikoxides, aryloxides, anionic species etc.;
  • PCy can be N-heterocyclcic carbene (NHC), and mixed NHC/PR 3 combinations; either of the PCy3 can be any 2-electron donor.
  • the present invention includes a synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts comprising a cross metathesis reaction between (L 1 )Ru(L 2 )(3-phenylindenylid-l-ene)Cl (where Lj and L can be two- electron donors) and an olefin.
  • At least one of the following ruthenium olefin metathesis catalysts is preferably isolated:
  • AU measurements disclosed herein are at standard temperature and pressure, at sea level on Earth, unless indicated otherwise.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts relies on the cross metathesis reaction between (L1)Ru(L2)(3-phenylindenylid-1-ene)Cl2 (where L1 and L2 can be two-electron donors) and an olefin. This method leads to the isolation of numerous ruthenium olefin metathesis catalysts.

Description

TITLE OF THE INVENTION "Preparation of Ruthenium-based Olefin Metathesis Catalysts"
INVENTOR: NOLAN, Ph.D., Steven, P. a Canadian citizen, of 6196 Chatham Drive, Apt. 153, New Orleans, LA 70122, US
ASSIGNEE: University of New Orleans Research & Technology Foundation, Inc. (a non-profit Louisiana, US, corporation), New Orleans, LA, US CROSS-REFERENCE TO RELATED APPLICATIONS
Priority of my prior US provisional patent application serial no. 60/479,771, filed 19 June 2003, incorporated herein by reference, is hereby claimed. STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT Not applicable
REFERENCE TO A "MICROFICHE APPENDIX"
Not applicable BACKGROUND OF THE INVENTION
1. Field of the Invention The present invention relates to olefin metathesis. More particularly, the present invention relates to synthesis of olefin metathesis catalysts.
2. General Background of the Invention
The advent of well-defined, highly reactive catalysts for olefin metathesis (ring-closing metathesis, RCM; ring-opening metathesis polymerization, ROMP; cross metathesis, CM; and their combinations) has made this technique a powerful tool in organic synthesis and polymer chemistry.1 Metal-carbene complexes of the type (PCy3)2Ru(=C(H)Ph)Cl2 (l)2, and its analogues modified with nucleophilic carbenes (PCy3)Ru(IMes)(=C(H)Ph)Cl23 (2), and (PCy3)Ru(SIMes)(=C(H)Ph)Cl2 (3)4 where IMes = l,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene and SIMes= 1,3- bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene, are highly efficient catalyst precursors. The inventor and his colleagues have shown that the complexes of unsaturated "Cα" ligands other than the alkylidenes such as (PCy )2Ru(3- phenylindenylid-l-ene)Cl2 (4) and (PCy3)( es)Ru(3-phenylindenylid-l-ene)Cl2 (5) are also active catalyst precursors in the ring-closing metathesis of dienes (Figure l).5
Figure imgf000003_0001
2 3
Figure imgf000003_0002
Figure imgf000003_0003
IMes SIMes
In its most widely used preparation, complex 1 has been synthesized by reaction of RuCl2(PPh3) with diazo compound according to eq. 1.
Figure imgf000003_0004
Complexes 4 and 5 are of particular interest since they are easily synthesized from RuCl2(PPh )3 and an alkyn-ol followed by simple ligand substitution reactions according to eq. 2.
Figure imgf000004_0001
This unusual rearrangement of an alkyn-ol into an indenylidene results in ruthenium complexes that are quite active in a number of olefin metathesis transformations. The following US Patents are incorporated herein by reference:
US Patent 6,403,802 Use of catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in amination reactions
US Patent 6,403,801 Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene of imidazolidine-2-ylidene in Suzuki coupling reactions
US Patent 6,369,265 Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in Kumada coupling reactions US Patent 6,362,357 Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions
US Patent 6,316,380 Catalyst system comprising transition metal and imidazoline-2- ylidene or imidazolidine-2-ylidene.
US Patent 6,586,599 Catalyzed coupling reactions of aryl halides with silanes; US Patent 6,583,307 Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system;
US Patent 6,403,802 Use of catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in amination reactions; US Patent 6,403,801 Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene of imidazolidine-2-ylidene in suzuki coupling reactions;
US Patent 6,369,265 Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in kumada coupling reactions: US Patent 6,362,357 Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions;
US Patent 6,316,380 Catalyst system comprising transition metal and imidazoline-2- ylidene or imidazolidine-2-ylidene; US Patent 5,110,948 Organosamarium catalysts for the hydroamination of olefins;
US Patent Application 20020198423 Al Convenient and efficient suzuki-miyaura cross-coupling catalyzed by a palladium/diazabutadiene system ;
United States Patent Application 20020173650 Al Metal complexes for hydro genation of unsaturated compounds; All of my prior US patent applications are incorporated herein by reference, including Serial Nos. 09/392,869, 09/507,958, 09/907,526, 10/011,680 (application published as US2002/0173650), 60/407,073.
BRIEF SUMMARY OF THE INVENTION
The present invention includes a process for the preparation of ruthenium- based olefin metathesis catalysts. The inventor has discovered that Ru-carbene complexes can be made from the Ru-indenylidene complex by cross metathesis. Other prior art routes are described above in the Background of the Invention.
The present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising making Ru-carbene complexes from a Ru-indenylidene complex by cross metathesis. Preferably, the process includes providing a Ru-indenylidene complex and an excess of an olefin.
The present invention includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising eq. 3 or a process similar to eq. 3, with one or more of the following variations: in place of CI one could use other halides, pseudohalides, alkoxides, aryloxides, anionic species etc.;
PCy3 can be N-heterocyclcic carbene (NHC), and mixed NHC/PR3 combinations; either of the PCy3 can be any 2-electron donor. The present invention includes a synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts comprising a cross metathesis reaction between (L1)Ru(L2)(3-phenylindenylid-l-ene)Cl2 (where Li and L2 can be two- electron donors) and an olefin. In any process or method of the present invention, at least one of the following ruthenium olefin metathesis catalysts is preferably isolated:
RuCl2(PCy3)2 (C(H)R), RuCl2(PCy3)(IMes) (C(H)R) where IMes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PCy3)(SIMes) (C(H)R) where SIMes is bis( 2,4,6 trimethylphenyl imidazolidine, RuCl2(pyridine)2 (L)(C(H)R) where L= Mes, S es, RuCl2(PPh3)(IMes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PPh3)(S es) (C(H)R) where SIMes is bis( 2,4,6 trimethylphenyl imidazolidine, where R = Ph, vinyl, etc.
Though a specific example is shown in the Detailed Description, the scope of the present invention includes general ancillary ligands (in place of CI one could use other halides, pseudohalides, aikoxides, aryloxides, anionic species etc.); PCy3 can be N-heterocyclcic carbene (NHC), and mixed NHC/PR combinations; in general either of the PCy can be any 2-electron donor.
DETAILED DESCRIPTION OF THE INVENTION
To further capitalize on the activity of the indenylidene complexes, the present inventor reasoned that complex 1 could be synthesized via a cross metathesis reaction according to eq. 3 eliminating the need for hazardous handling of a diazo reagent.
Figure imgf000006_0001
The described method appears general and various alkylidenes can be synthesized in this manner.
Though a specific example is shown above, the scope of the present invention includes general ancillary ligands (in place of CI one could use other halides, pseudohalides, aikoxides, aryloxides, anionic species etc.); PCy3 can be N- heterocyclcic carbene (NHC), and mixed NHC/PR3 combinations; in general either of the PCy3 can be any 2-electron donor.
The present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, including those mentioned above in the Background of the Invention. The inventor has discovered that Ru-carbene complexes can be made from the Ru-indenylidene complex by cross metathesis.
The present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising making Ru-carbene complexes from a Ru-indenylidene complex by cross metathesis. Preferably, the process includes providing a Ru-indenylidene complex and an excess of an olefin. The present invention includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising eq. 3 or a process similar to eq. 3, with one or more of the following variations: in place of CI one could use other halides, pseudohalides, aikoxides, aryloxides, anionic species etc.;
PCy can be N-heterocyclcic carbene (NHC), and mixed NHC/PR3 combinations; either of the PCy3 can be any 2-electron donor. The present invention includes a synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts comprising a cross metathesis reaction between (L1)Ru(L2)(3-phenylindenylid-l-ene)Cl (where Lj and L can be two- electron donors) and an olefin.
In any process or method of the present invention, at least one of the following ruthenium olefin metathesis catalysts is preferably isolated:
RuCl2(PCy3)2 (C(H)R), RuCl2(PCy3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PCy3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, RuCl2(pyridine)2 (L)(C(H)R) where L= Mes, SMes, RuCl2(PPh3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PPh3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, where R = Ph, vinyl, etc.
References and Notes (all incorporated herein by reference)
(1) (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450 and references therein, (b) Ivin, K. J. Mol. Catal. A: Chem., 1998, 133, 1-16. (c) Randall, M. L.; Snapper, M. L. J Mol. Catal. A: Chem., 1998, 133, 29-40. (d) Tmka, T.; Grubbs, R. H. Ace. Chem. Res. 2001, 34, 18-29. (e) Jafarpour, L.; Nolan, S. P. J. Organomet. Chem. 2001, 617, 11-21.
(2) (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039-2041. (b) Schwab, P.; Grubbs, R. H.; Ziller. j. W. J. Am. Chem. Soc. 1996,118, 100-110. (c) Diaz, E. L.; Nguyen, S. T.; Gmbbs, R. H. J. Am. Chem. Soc. 1991,119, 3887-3897 and references cited.
(3) (a) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678. (b) Huang, J.; Schanz, H. -J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375-5380. (c) SchoU, M. ; Tmka, T. M.; Morgan, J. P.; Gmbbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250. (d) Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4748- 4790. (e) SchoU, M.; Ding, S.; Lee, C. W.; Gmbbs, R. H. Org. Lett. 1999, 1, 1751- 1753. (f) Furstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H. -J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204-2207. (g) Briot, A.; Bujard, M.; Gouvemeur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517-1519.
(4) (a) SchoU, M.; Ding, S.; Lee, C. W.; Gmbbs, R. H. Organic Lett. 1999, 1, 953- 956. (b) Chatterjee, A. K.; Morgan, J. P.; SchoU, M.; Gmbbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783-3784. (c) Chatterjee, A. K.; Gmbbs, R. H. Organic Lett. 1999, 1, 1751-1753.
(5) (a) Furstner, A.; Hill, A. F.; Liebl, M.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602. (b) Jafarpour, L.; Schanz, H. -J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5416-5419.
AU measurements disclosed herein are at standard temperature and pressure, at sea level on Earth, unless indicated otherwise.
The foregoing embodiments are presented by way of example only; the scope of the present invention is to be limited only by the following claims.

Claims

CLAMS
1. A process for the preparation of ruthenium-based olefin metathesis catalysts, comprising making Ru-carbene complexes from a Ru-indenylidene complex by cross metathesis.
2. The process of claim 1, comprising: providing a Ru-indenylidene complex and an excess of an olefin.
3. A process for the preparation of ruthenium-based olefin metathesis catalysts, comprising eq. 3.
4. A process for the preparation of rathenium-based olefin metathesis catalysts, comprising a process similar to eq. 3, with one or more of the following variations: in place of CI one could use other halides, pseudohalides, aikoxides, aryloxides, anionic species etc.;
PCy3 can be N-heterocyclcic carbene (NHC), and mixed NHC/PR3 combinations; either of the PCy3 can be any 2-electron donor.
5. A synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts comprising a cross metathesis reaction between (Lι)Ru(L2)(3- phenylindenylid-l-ene)Cl2 (where Li and L2 can be two-electron donors) and an olefin.
6. The method of claim 5, wherein at least one of the following ruthenium olefin metathesis catalysts is isolated:
RuCl2(PCy3)2 (C(H)R), RuCl2(PCy3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PCy3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, RuCl2(pyridine)2 (L)(C(H)R) where L= Mes, SMes, RuCl2(PPh3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PPh3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, where R = Ph, vinyl, etc.
7. The process of claim 4, wherein at least one of the following ruthenium olefin metathesis catalysts is isolated:
RuCl2(PCy3)2 (C(H)R), RuCl2(PCy3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PCy3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, RuCl2(pyridine)2 (L)(C(H)R) where L= Mes, SMes, RuCl2(PPh3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PPh3)(SMes) (C(H)R) where SIMes is bis( 2,4,6 trimethylphenyl imidazolidine, where R = Ph, vinyl, etc.
8. The process of claim 3, wherein at least one of the following ruthenium olefin metathesis catalysts is isolated: RuCl2(PCy3)2 (C(H)R), RuCl2(PCy3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PCy3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, RuCl2(pyridine)2 (L)(C(H)R) where L= Mes, SMes, RuCl2(PPh3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PPh3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, where R = Ph, vinyl, etc.
9. The process of claim 2, wherein at least one of the following ruthenium olefin metathesis catalysts is isolated:
RuCl2(PCy3)2 (C(H)R), RuCl2(PCy3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PCy3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, RuCl2(pyridine)2 (L)(C(H)R) where L= Mes, SMes, RuCl2(PPh3)(Mes) (C(H)R) where Mes is bis( 2.4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PPh3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, where R = Ph, vinyl, etc.
10. The process of claim 1, wherein at least one of the following rathenium olefin metathesis catalysts is isolated:
RuCl2(PCy3)2 (C(H)R), RuCl2(PCy3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PCy3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, RuCl2(pyridine)2 (L)(C(H)R) where L= Mes, SMes, RuCl2(PPh3)(Mes) (C(H)R) where Mes is bis( 2,4,6 trimethylphenyl imidazol-2-ylidene , RuCl2(PPh3)(SMes) (C(H)R) where SMes is bis( 2,4,6 trimethylphenyl imidazolidine, where R = Ph, vinyl, etc.
11. The invention(s) substantially as shown and/or described herein.
PCT/US2004/019712 2003-06-19 2004-06-21 Preparation of ruthenium-based olefin metathesis catalysts Ceased WO2004112951A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04755714A EP1654060A4 (en) 2003-06-19 2004-06-21 Preparation of ruthenium-based olefin metathesis catalysts

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47977103P 2003-06-19 2003-06-19
US60/479,771 2003-06-19

Publications (2)

Publication Number Publication Date
WO2004112951A2 true WO2004112951A2 (en) 2004-12-29
WO2004112951A3 WO2004112951A3 (en) 2005-04-21

Family

ID=33539218

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/019712 Ceased WO2004112951A2 (en) 2003-06-19 2004-06-21 Preparation of ruthenium-based olefin metathesis catalysts

Country Status (3)

Country Link
US (1) US7205424B2 (en)
EP (1) EP1654060A4 (en)
WO (1) WO2004112951A2 (en)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2027920A1 (en) 2007-08-21 2009-02-25 Lanxess Deutschland GmbH Catalysts for metathesis reactions
DE102007039526A1 (en) 2007-08-21 2009-02-26 Lanxess Deutschland Gmbh Catalyst systems and their use for metathesis reactions
DE102007039695A1 (en) 2007-08-22 2009-02-26 Lanxess Deutschland Gmbh New ruthenium- and osmium-carbene-complex catalysts, which are bonded with chiral carbon atoms or over double bonds at a catalyst base skeleton, useful e.g. in metathesis-reactions, preferably in ring closing metathesis reactions
DE102007039525A1 (en) 2007-08-21 2009-02-26 Lanxess Deutschland Gmbh Process for metathesis degradation of nitrile rubber
DE102007039527A1 (en) 2007-08-21 2009-02-26 Lanxess Deutschland Gmbh New ruthenium- and osmium-carbene-complex catalysts, which are bonded with chiral carbon atoms or over double bonds at a catalyst base skeleton, useful e.g. in metathesis-reactions, preferably in ring closing metathesis reactions
EP2145681A1 (en) 2008-07-08 2010-01-20 Lanxess Deutschland GmbH Method for the reduction of the molecular weight of nitrile rubber
WO2010066959A1 (en) 2008-12-10 2010-06-17 Ifp Catalytic composition and method for the metathesis of unsaturated fat
WO2011091980A1 (en) 2010-01-29 2011-08-04 Umicore Ag & Co. Kg Process for preparation of ruthenium-based carbene catalysts with chelating alkylidene ligands
EP2395034A1 (en) 2010-06-14 2011-12-14 LANXESS Deutschland GmbH Blends from partially hydrated nitrile rubber and silicon rubber, vulcanisable mixtures based on same and vulcanisates
EP2418225A1 (en) 2010-08-09 2012-02-15 LANXESS Deutschland GmbH Partially hydrated nitrile rubbers
EP2428269A1 (en) 2010-09-08 2012-03-14 Bergen Teknologioverføring AS Novel olefin metathesis catalysts
EP2484700A1 (en) 2011-02-04 2012-08-08 LANXESS Deutschland GmbH Functionalised nitrile rubbers and their manufacture
WO2013057295A2 (en) 2011-10-21 2013-04-25 Lanxess Deutschland Gmbh Catalyst compositions and their use for hydrogenation of nitrile rubber
WO2013057286A1 (en) 2011-10-21 2013-04-25 Lanxess Deutschland Gmbh Catalyst compositions and their use for hydrogenation of nitrile rubber
WO2013098052A2 (en) 2011-12-28 2013-07-04 Lanxess Deutschland Gmbh Metathesis of nitrile rubbers in the presence of transition metal complex catalysts
WO2013098056A1 (en) 2011-12-28 2013-07-04 Lanxess Deutschland Gmbh Purification of optionally hydrogenated nitrile rubber
WO2014108071A1 (en) 2013-01-10 2014-07-17 Guang Ming Innovation Company (Wuhan) Catalyst complexes with carbene ligand and method for making same and use in metathesis reaction
WO2016000242A1 (en) 2014-07-03 2016-01-07 Guang Ming Innovation Company (Wuhan) Group 8 transition metal catalysts and method for making same and process for use of same in metathesis reaction
EP3115368A1 (en) 2015-07-10 2017-01-11 Bergen Teknologioverforing AS Improved olefin metathesis catalysts

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1603857A4 (en) * 2003-01-13 2006-05-17 Cargill Inc Method for making industrial chemicals
WO2007081987A2 (en) * 2006-01-10 2007-07-19 Elevance Renewable Sciences, Inc. Method of making hydrogenated metathesis products
US20070250327A1 (en) * 2006-04-24 2007-10-25 Shad Hedy System and method for used vehicle valuation based on actual transaction data provided by industry participants
WO2008008440A2 (en) * 2006-07-12 2008-01-17 Elevance Renewable Sciences, Inc. Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like
WO2008010961A2 (en) 2006-07-13 2008-01-24 Elevance Renewable Sciences, Inc. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
WO2008048520A2 (en) 2006-10-13 2008-04-24 Elevance Renewable Sciences, Inc. Methods of making organic compounds by metathesis and hydrocyanation
EP2076484B1 (en) 2006-10-13 2020-01-08 Elevance Renewable Sciences, Inc. Synthesis of terminal alkenes from internal alkenes via olefin metathesis
DK2121546T3 (en) * 2006-10-13 2018-03-12 Elevance Renewable Sciences Process for preparing omega-dicarboxylic acid olefin derivative by metathesis
ES2569483T3 (en) 2007-06-21 2016-05-11 Amgen Inc. Methods to synthesize cinacalcet and salts thereof
WO2009004727A1 (en) * 2007-07-04 2009-01-08 Fujitsu Limited Encoding apparatus, encoding method and encoding program
EP2143489A1 (en) * 2008-07-08 2010-01-13 Lanxess Deutschland GmbH Catalyst systems and their use in metathesis reactions
EP2255877B1 (en) 2009-05-07 2014-09-24 Umicore AG & Co. KG Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands
RU2506026C2 (en) * 2009-09-16 2014-02-10 Колгейт-Палмолив Компани System and method for oral care
US8237003B2 (en) * 2009-11-09 2012-08-07 Exxonmobil Chemical Patents Inc. Metathesis catalyst and process for use thereof
US9024034B2 (en) * 2009-11-09 2015-05-05 Exxonmobil Chemical Patents Inc. Metathesis catalysts and processes for use thereof
US8329921B2 (en) 2009-11-09 2012-12-11 Exxonmobil Chemical Patents Inc. Metathesis catalyst and process for use thereof
US8809563B2 (en) 2009-11-09 2014-08-19 Exxonmobil Chemical Patents Inc. Metathesis catalyst and process for use thereof
ES2496985T3 (en) 2009-12-23 2014-09-22 Colgate-Palmolive Company Oral and dental hygiene system
PH12012500882A1 (en) 2009-12-23 2013-01-07 Colgate Palmolive Co Oral care system, kit and method
KR101414966B1 (en) 2009-12-23 2014-07-04 콜게이트-파아므올리브캄파니 Oral care system, kit and method
KR101528395B1 (en) 2009-12-23 2015-06-11 콜게이트-파아므올리브캄파니 Oral care system
EP2533899A4 (en) * 2010-02-12 2013-08-07 Exxonmobil Chem Patents Inc Metathesis catalyst and process for use thereof
US8227371B2 (en) 2010-09-24 2012-07-24 Exxonmobil Chemical Patents Inc. Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof
PH12013501082A1 (en) 2010-12-15 2013-07-08 Colgate Palmolive Co Oral care dispenser
US9181360B2 (en) 2011-08-12 2015-11-10 Exxonmobil Chemical Patents Inc. Polymers prepared by ring opening / cross metathesis
AU2015381790B2 (en) 2015-02-02 2018-10-04 Colgate-Palmolive Company Oral care system and oral care material dispenser
HUE073559T2 (en) 2017-02-17 2026-01-28 Provivi Inc Synthesis of pheromones and related materials via olefin metathesis
JP7495934B2 (en) 2018-12-10 2024-06-05 プロビビ インコーポレイテッド Methods for synthesizing conjugated diene pheromones and related compounds
US11891517B2 (en) 2020-03-10 2024-02-06 Exxonmobil Chemical Patents Inc. Wax compositions comprising linear olefin dimers or hydrogenated variants thereof and methods for production thereof

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3928699A (en) 1971-07-13 1975-12-23 Huyck Corp Papermakers felts
US5110948A (en) 1988-12-28 1992-05-05 Northwestern University Organosamarium catalysts for the hydroamination of olefins
US6316380B1 (en) 1998-09-10 2001-11-13 University Of New Orleans Research & Technology Foundation Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene
US6362357B1 (en) 1999-02-22 2002-03-26 University Of New Orleans Research & Technology Foundation Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions
US6369265B1 (en) 1999-09-16 2002-04-09 University Of New Orleans Research & Technology Foundation Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in kumada coupling reactions
US6403802B1 (en) 1998-09-10 2002-06-11 University Of New Orleans Research & Technology Foundation Use of catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in amination reactions
US6403801B1 (en) 1999-02-22 2002-06-11 University Of New Orleans Research & Technology Foundation Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene of imidazolidine-2-ylidene in suzuki coupling reactions
US20020173650A1 (en) 2000-12-04 2002-11-21 Nolan Steven P. Metal complexes for hydrogenation of unsaturated compounds
US20020198423A1 (en) 2001-03-07 2002-12-26 Nolan Steven P. Convenient and efficient suzuki-miyaura cross-coupling catalyzed by a palladium/diazabutadiene system
US6586599B1 (en) 2000-04-20 2003-07-01 University Of New Orleans Research And Technology Foundation Catalyzed coupling reactions of aryl halides with silanes

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5312940A (en) * 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
US5939504A (en) * 1995-12-07 1999-08-17 Advanced Polymer Technologies Method for extending the pot life of an olefin metathesis polymerization reaction
AU2412599A (en) 1997-12-04 1999-06-28 Ciba Specialty Chemicals Holding Inc. Heterocyclyl ligand containing ruthenium and osmium catalysts
US6175047B1 (en) * 1997-12-26 2001-01-16 Takasago International Corporation Ruthenium metathesis catalyst and method for producing olefin reaction product by metathesis reaction using the same
DE19815275B4 (en) * 1998-04-06 2009-06-25 Evonik Degussa Gmbh Alkylidene complexes of ruthenium with N-heterocyclic carbene ligands and their use as highly active, selective catalysts for olefin metathesis
DE19820652A1 (en) * 1998-05-08 1999-11-11 Basf Ag Cationic ruthenium complexes used as catalyst for metathesis reactions
US6900347B2 (en) * 1998-09-01 2005-05-31 Tilliechem, Inc. Impurity inhibition in olefin metathesis reactions
DE60039166D1 (en) * 1999-03-31 2008-07-24 California Inst Of Techn COORDINATED RUTHENIUM METAL ALKYLIDE COMPLEXES WITH TRIAZOLYDIN LIGANDS HAVE THE HIGH OLEFIN METATHESE ACTIVITY
WO2002020535A1 (en) * 2000-09-05 2002-03-14 California Institute Of Technology Highly active metathesis catalysts generated in situ from inexpensive and air stable precursors
EP1379485A4 (en) * 2001-03-30 2005-08-31 California Inst Of Techn CROSSED METATHESIS WITH OPENING OF THE CYCLO-OLEFINS SELECTIVE CYCLE
US6613910B2 (en) 2001-04-02 2003-09-02 California Institute Of Technology One-pot synthesis of group 8 transition metal carbene complexes useful as olefin metathesis catalysts
US7683180B2 (en) * 2001-04-16 2010-03-23 California Institute Of Technology Group 8 transition metal carbene complexes as enantionselective olefin metathesis catalysts
CA2441821A1 (en) * 2001-04-16 2002-10-24 Yeda Research And Development Co. Ltd. New method for the preparation of metal carbene complexes
US6872792B2 (en) 2001-06-25 2005-03-29 Lord Corporation Metathesis polymerization adhesives and coatings
US6818586B2 (en) * 2001-08-01 2004-11-16 Cymetech, Llp Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
US6620955B1 (en) * 2001-11-15 2003-09-16 Richard L. Pederson Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
PL199412B1 (en) * 2002-10-15 2008-09-30 Boehringer Ingelheim Int Ruthenium new complexes as (pre) catalytic agents of permutation reaction, new derivatives of 2-alkoxy-5-nitrostyrene as intermediate compounds and method of their receiving

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3928699A (en) 1971-07-13 1975-12-23 Huyck Corp Papermakers felts
US5110948A (en) 1988-12-28 1992-05-05 Northwestern University Organosamarium catalysts for the hydroamination of olefins
US6316380B1 (en) 1998-09-10 2001-11-13 University Of New Orleans Research & Technology Foundation Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene
US6403802B1 (en) 1998-09-10 2002-06-11 University Of New Orleans Research & Technology Foundation Use of catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in amination reactions
US6362357B1 (en) 1999-02-22 2002-03-26 University Of New Orleans Research & Technology Foundation Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions
US6403801B1 (en) 1999-02-22 2002-06-11 University Of New Orleans Research & Technology Foundation Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene of imidazolidine-2-ylidene in suzuki coupling reactions
US6369265B1 (en) 1999-09-16 2002-04-09 University Of New Orleans Research & Technology Foundation Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in kumada coupling reactions
US6586599B1 (en) 2000-04-20 2003-07-01 University Of New Orleans Research And Technology Foundation Catalyzed coupling reactions of aryl halides with silanes
US20020173650A1 (en) 2000-12-04 2002-11-21 Nolan Steven P. Metal complexes for hydrogenation of unsaturated compounds
US20020198423A1 (en) 2001-03-07 2002-12-26 Nolan Steven P. Convenient and efficient suzuki-miyaura cross-coupling catalyzed by a palladium/diazabutadiene system
US6583307B2 (en) 2001-03-07 2003-06-24 University Of New Orleans Research And Technology Foundation, Inc. Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
GANDLEMAN: "A New General Method for the Preparation of Metal Carbene Complexes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 123, no. 22, 2001, pages 5372 - 5373
GRUBBS, R. H.; CHANG, S., TETRAHEDRON, vol. 54, 1998, pages 4413 - 4450
IVIN, K., J. MOL. CATAL. A: CHEM., vol. 133, 1998, pages 1 - 16
JAFARPOUR, L.; NOLAN, S. P., J. ORGANOMET. CHEM., vol. 617, 2001, pages 17 - 27
RANDALL, M. L.; SNAPPER, M. L., J. MOL. CATAL. A: CHEM., vol. 133, 1998, pages 29 - 40
SCHWAB, P. ET AL., ANGEW. CHEM. INT. ED. ENGL., vol. 34, 1995, pages 2039 - 2041
SCHWAB, P.; GRUBBS, R. H.; ZILLER. J. W., J. AM. CHEM.
SCHWAB: "Synthesis and Applications ofRuCl- 2(=CHR!)(Pr3)2: The Influence of the Alkylidene Moiety on Metathesis Activity", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 118, no. 1/5, 1996, pages 100 - 110
See also references of EP1654060A4
TRNKA, T.; GRUBBS, R. H., ACE. CHEM. RES., vol. 34, 2001, pages 18 - 29
TRNKA: "The Development of L2X2Ru=CHR Olefin Metathesis Catalysts: An Organometallic Success Story", ACCOUNTS OF CHEMICAL RESEARCH, vol. 34, no. 1, 2000, pages 18 - 29

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2027920A1 (en) 2007-08-21 2009-02-25 Lanxess Deutschland GmbH Catalysts for metathesis reactions
DE102007039526A1 (en) 2007-08-21 2009-02-26 Lanxess Deutschland Gmbh Catalyst systems and their use for metathesis reactions
DE102007039525A1 (en) 2007-08-21 2009-02-26 Lanxess Deutschland Gmbh Process for metathesis degradation of nitrile rubber
DE102007039527A1 (en) 2007-08-21 2009-02-26 Lanxess Deutschland Gmbh New ruthenium- and osmium-carbene-complex catalysts, which are bonded with chiral carbon atoms or over double bonds at a catalyst base skeleton, useful e.g. in metathesis-reactions, preferably in ring closing metathesis reactions
US8507398B2 (en) 2007-08-21 2013-08-13 Lanxess Deutschland Gmbh Catalysts for metathesis reactions
DE102007039695A1 (en) 2007-08-22 2009-02-26 Lanxess Deutschland Gmbh New ruthenium- and osmium-carbene-complex catalysts, which are bonded with chiral carbon atoms or over double bonds at a catalyst base skeleton, useful e.g. in metathesis-reactions, preferably in ring closing metathesis reactions
EP2145681A1 (en) 2008-07-08 2010-01-20 Lanxess Deutschland GmbH Method for the reduction of the molecular weight of nitrile rubber
JP2010018801A (en) * 2008-07-08 2010-01-28 Lanxess Deutschland Gmbh Catalyst system and use of the same for metathesis reaction
WO2010066959A1 (en) 2008-12-10 2010-06-17 Ifp Catalytic composition and method for the metathesis of unsaturated fat
WO2011091980A1 (en) 2010-01-29 2011-08-04 Umicore Ag & Co. Kg Process for preparation of ruthenium-based carbene catalysts with chelating alkylidene ligands
EP2361683A1 (en) 2010-01-29 2011-08-31 Umicore AG & Co. KG Process for preparation of ruthenium-based carbene catalysts with chelating alkylidene ligands
US9278345B2 (en) 2010-01-29 2016-03-08 Umicore Ag & Co. Kg Process for preparation of ruthenium-based carbene catalysts with chelating alkylidene ligands
EP2395034A1 (en) 2010-06-14 2011-12-14 LANXESS Deutschland GmbH Blends from partially hydrated nitrile rubber and silicon rubber, vulcanisable mixtures based on same and vulcanisates
WO2011157711A1 (en) 2010-06-14 2011-12-22 Lanxess Deutschland Gmbh Blends of partially hydrogenated nitrile rubber and silicone rubber, vulcanizable mixtures and vulcanizates based thereon
EP2418225A1 (en) 2010-08-09 2012-02-15 LANXESS Deutschland GmbH Partially hydrated nitrile rubbers
WO2012019978A1 (en) 2010-08-09 2012-02-16 Lanxess Deutschland Gmbh Partially hydrogenated nitrile rubbers
EP2428269A1 (en) 2010-09-08 2012-03-14 Bergen Teknologioverføring AS Novel olefin metathesis catalysts
WO2012032131A1 (en) 2010-09-08 2012-03-15 Bergen Teknologioverføring As Novel olefin metathesis catalysts
EP2484700A1 (en) 2011-02-04 2012-08-08 LANXESS Deutschland GmbH Functionalised nitrile rubbers and their manufacture
WO2012104183A1 (en) 2011-02-04 2012-08-09 Lanxess Deutschland Gmbh Functionalised nitrile rubbers and the production thereof
WO2013057295A2 (en) 2011-10-21 2013-04-25 Lanxess Deutschland Gmbh Catalyst compositions and their use for hydrogenation of nitrile rubber
WO2013057286A1 (en) 2011-10-21 2013-04-25 Lanxess Deutschland Gmbh Catalyst compositions and their use for hydrogenation of nitrile rubber
WO2013098052A2 (en) 2011-12-28 2013-07-04 Lanxess Deutschland Gmbh Metathesis of nitrile rubbers in the presence of transition metal complex catalysts
WO2013098056A1 (en) 2011-12-28 2013-07-04 Lanxess Deutschland Gmbh Purification of optionally hydrogenated nitrile rubber
WO2014108071A1 (en) 2013-01-10 2014-07-17 Guang Ming Innovation Company (Wuhan) Catalyst complexes with carbene ligand and method for making same and use in metathesis reaction
EP2943499A4 (en) * 2013-01-10 2016-08-10 Guangming Innovation Company Wuhan CATALYST COMPLEXES WITH CARBENE LIGAND, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF IN METATHESIS REACTION
WO2016000242A1 (en) 2014-07-03 2016-01-07 Guang Ming Innovation Company (Wuhan) Group 8 transition metal catalysts and method for making same and process for use of same in metathesis reaction
EP3115368A1 (en) 2015-07-10 2017-01-11 Bergen Teknologioverforing AS Improved olefin metathesis catalysts
WO2017009232A1 (en) 2015-07-10 2017-01-19 Bergen Teknologioverføring As Improved olefin metathesis catalysts
US10265691B2 (en) 2015-07-10 2019-04-23 Bergen Teknologioverforing As Olefin metathesis catalysts

Also Published As

Publication number Publication date
US20050026774A1 (en) 2005-02-03
US7205424B2 (en) 2007-04-17
WO2004112951A3 (en) 2005-04-21
EP1654060A4 (en) 2007-08-08
EP1654060A2 (en) 2006-05-10

Similar Documents

Publication Publication Date Title
WO2004112951A2 (en) Preparation of ruthenium-based olefin metathesis catalysts
Jafarpour et al. Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts
Katayama et al. Convenient Routes to Vinylideneruthenium Dichlorides with Basic and Bulky Tertiary Phosphine Ligands (PPr i 3 and PCy3)
Jafarpour et al. Simple and Convenient Synthetic Procedure Leading to Ruthenium Olefin Metathesis Catalysts Bearing the N, N ‘-Bis (mesityl) imidazol-2-ylidene (IMes) Ligand
Jafarpour et al. Improved one-pot synthesis of second-generation ruthenium olefin metathesis catalysts
Ackermann et al. Ruthenium carbene complexes with imidazolin-2-ylidene ligands allow the formation of tetrasubstituted cycloalkenes by RCM
Jafarpour et al. Simply assembled and recyclable polymer-supported olefin metathesis catalysts
Yao et al. Immobilization of the Grubbs second-generation ruthenium-carbene complex on poly (ethylene glycol): a highly reactive and recyclable catalyst for ring-closing and cross-metathesis
Deshmukh et al. Alkene metathesis: the search for better catalysts
Michrowska et al. A green catalyst for green chemistry: Synthesis and application of an olefin metathesis catalyst bearing a quaternary ammonium group
Buchmeiser Recent advances in the synthesis of supported metathesis catalysts
Copéret et al. Strategies to immobilize well‐defined olefin metathesis catalysts: supported homogeneous catalysis vs. surface organometallic chemistry
Samojłowicz et al. Ruthenium-based olefin metathesis catalysts bearing N-heterocyclic carbene ligands
Garber et al. Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts
Śledź et al. Olefin metathesis in ionic liquids
Varray et al. New soluble-polymer bound ruthenium carbene catalysts: Synthesis, characterization, and application to ring-closing metathesis
Schowner et al. Cationic tungsten-oxo-alkylidene-N-heterocyclic carbene complexes: highly active olefin metathesis catalysts
Camm et al. Tandem ROMP− hydrogenation with a third-generation grubbs catalyst
KR101291468B1 (en) Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions
Dharmasena et al. N-heterocyclic carbenes as activating ligands for hydrogenation and isomerization of unactivated olefins
Schoeps et al. Batchwise and continuous organophilic nanofiltration of Grubbs‐type olefin metathesis catalysts
Karamé et al. Tailored Ru‐NHC Heterogeneous Catalysts for Alkene Metathesis
EP1904424A2 (en) The use of a phosphorus containing ligand and a cyclic organic ligand in a transition metal compound
Severin Asymmetric Halogeno‐Bridged Complexes: New Reagents in Organometallic Synthesis and Catalysis
Michrowska et al. Quest for the ideal olefin metathesis catalyst

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
REEP Request for entry into the european phase

Ref document number: 2004755714

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2004755714

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2004755714

Country of ref document: EP