WO2006012046A3 - Preparation of aminophosphines - Google Patents

Preparation of aminophosphines Download PDF

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Publication number
WO2006012046A3
WO2006012046A3 PCT/US2005/021376 US2005021376W WO2006012046A3 WO 2006012046 A3 WO2006012046 A3 WO 2006012046A3 US 2005021376 W US2005021376 W US 2005021376W WO 2006012046 A3 WO2006012046 A3 WO 2006012046A3
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WO
WIPO (PCT)
Prior art keywords
asymmetric
formula
aminophosphines
preparation
contacting
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/US2005/021376
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French (fr)
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WO2006012046A2 (en
Inventor
Neil Warren Boaz
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.)
Eastman Chemical Co
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Eastman Chemical Co
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 Eastman Chemical Co filed Critical Eastman Chemical Co
Priority to EP05762763A priority Critical patent/EP1758845B1/en
Priority to DE602005011432T priority patent/DE602005011432D1/en
Priority to JP2007518136A priority patent/JP2008504262A/en
Publication of WO2006012046A2 publication Critical patent/WO2006012046A2/en
Publication of WO2006012046A3 publication Critical patent/WO2006012046A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • 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
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • B01J31/2495—Ligands comprising a phosphine-P atom and one or more further complexing phosphorus atoms covered by groups B01J31/1845 - B01J31/1885, e.g. phosphine/phosphinate or phospholyl/phosphonate ligands
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F17/00—Metallocenes
    • C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
    • 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
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/44—Allylic alkylation, amination, alkoxylation or analogues
    • 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
    • B01J2231/52—Isomerisation reactions
    • 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
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • 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
    • B01J2531/822—Rhodium
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)

Abstract

Disclosed is a process for the preparation of phosphine-aminophosphines that are useful in the formation of catalysts useful in carrying out a wide variety of reactions such as asymmetric hydrogenations, asymmetric reductions, asymmetric hydroborations, asymmetric olefin isomerizations, asymmetric hydrosilations, asymmetric allylations, asymmetric conjugate additions, and asymmetric organometallic additions. The process comprises the steps of (1) contacting a compound of formula (2): R2P-L-NHR3 with phosphorus trihalide PX3 in the presence of an inert, organic solvent and an acid acceptor to produce intermediate compound having formula (3); (2) contacting intermediate compound (3) with a reactant having the formula R1-M1, R2-M1 or a mixture thereof.
PCT/US2005/021376 2004-06-25 2005-06-16 Preparation of aminophosphines Ceased WO2006012046A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05762763A EP1758845B1 (en) 2004-06-25 2005-06-16 Preparation of aminophosphines
DE602005011432T DE602005011432D1 (en) 2004-06-25 2005-06-16 PREPARATION OF AMINOPHOSPHINES
JP2007518136A JP2008504262A (en) 2004-06-25 2005-06-16 Production of aminophosphine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/876,492 US6906213B1 (en) 2004-06-25 2004-06-25 Preparation of aminophosphines
US10/876,492 2004-06-25

Publications (2)

Publication Number Publication Date
WO2006012046A2 WO2006012046A2 (en) 2006-02-02
WO2006012046A3 true WO2006012046A3 (en) 2006-04-27

Family

ID=34634716

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/021376 Ceased WO2006012046A2 (en) 2004-06-25 2005-06-16 Preparation of aminophosphines

Country Status (6)

Country Link
US (1) US6906213B1 (en)
EP (1) EP1758845B1 (en)
JP (1) JP2008504262A (en)
AT (1) ATE416154T1 (en)
DE (1) DE602005011432D1 (en)
WO (1) WO2006012046A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6906212B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Phosphine-phosphoramidite compounds
US6906213B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Preparation of aminophosphines

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002026750A2 (en) * 2000-09-29 2002-04-04 Eastman Chemical Company Phosphino-aminophosphines, catalyst complexes and enantioselective hydrogenation
WO2003082885A1 (en) * 2002-03-25 2003-10-09 Eastman Chemical Company Phosphinometallocenylamides as novel ligands for asymmetric catalysis
US6906212B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Phosphine-phosphoramidite compounds
US6906213B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Preparation of aminophosphines
WO2005068478A1 (en) * 2004-01-14 2005-07-28 Phoenix Chemicals Limited Process for the production of asymmetric transformation catalysts
US6939981B1 (en) * 2004-06-25 2005-09-06 Eastman Chemical Company Ruthenium complexes of phosphine-aminophosphine ligands

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002026750A2 (en) * 2000-09-29 2002-04-04 Eastman Chemical Company Phosphino-aminophosphines, catalyst complexes and enantioselective hydrogenation
WO2003082885A1 (en) * 2002-03-25 2003-10-09 Eastman Chemical Company Phosphinometallocenylamides as novel ligands for asymmetric catalysis
WO2005068478A1 (en) * 2004-01-14 2005-07-28 Phoenix Chemicals Limited Process for the production of asymmetric transformation catalysts
WO2005068477A1 (en) * 2004-01-14 2005-07-28 Phoenix Chemicals Limited Metallocene-based chiral phosphine or arsine ligands
US6906212B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Phosphine-phosphoramidite compounds
US6906213B1 (en) * 2004-06-25 2005-06-14 Eastman Chemical Company Preparation of aminophosphines
US6939981B1 (en) * 2004-06-25 2005-09-06 Eastman Chemical Company Ruthenium complexes of phosphine-aminophosphine ligands

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
HU XIANG-PING ET AL: "Practical Rh(I)-catalyzed asymmetric hydrogenation of beta-(acylamino)acrylates using a new unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligand: crucial influence of an N-H proton in the ligand.", ORGANIC LETTERS, vol. 7, no. 3, 3 February 2005 (2005-02-03), pages 419 - 422, XP009057439, ISSN: 1523-7060 *
HU XIANG-PING ET AL: "Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: a new class of practical ligands for Rh-catalyzed asymmetric hydrogenation.", ORGANIC LETTERS, vol. 6, no. 20, 30 September 2004 (2004-09-30), pages 3585 - 3588, XP009057443, ISSN: 1523-7060 *
JIA X ET AL: "The synthesis of new chiral phosphine-phosphinites, phosphine-phosphoramidite, and phosphine-phosphite ligands and their applications in asymmetric hydrogenation", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 15, no. 14, 26 July 2004 (2004-07-26), pages 2273 - 2278, XP004523719, ISSN: 0957-4166 *
NOVIKOVA Z S ET AL: "Synthesis of di(heteroelement)-substituted enamines", JOURNAL OF GENERAL CHEMISTRY OF THE USSR, vol. 59, no. 10, 1989, pages 2134 - 2135, XP009057434 *
ZENG Q-H ET AL: "New unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligands derived from H8-BINOL for highly efficient Rh-catalyzed enantioselective hydrogenation", TETRAHEDRON: ASYMMETRY, PERGAMON, OXFORD, GB, vol. 16, no. 6, 21 March 2005 (2005-03-21), pages 1233 - 1238, XP004785968, ISSN: 0957-4166 *

Also Published As

Publication number Publication date
EP1758845A2 (en) 2007-03-07
WO2006012046A2 (en) 2006-02-02
ATE416154T1 (en) 2008-12-15
DE602005011432D1 (en) 2009-01-15
US6906213B1 (en) 2005-06-14
EP1758845B1 (en) 2008-12-03
JP2008504262A (en) 2008-02-14

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