WO2013135552A3 - Phosphinite und amidophosphinite als liganden in katalytischen reaktionen - Google Patents

Phosphinite und amidophosphinite als liganden in katalytischen reaktionen Download PDF

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Publication number
WO2013135552A3
WO2013135552A3 PCT/EP2013/054583 EP2013054583W WO2013135552A3 WO 2013135552 A3 WO2013135552 A3 WO 2013135552A3 EP 2013054583 W EP2013054583 W EP 2013054583W WO 2013135552 A3 WO2013135552 A3 WO 2013135552A3
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WO
WIPO (PCT)
Prior art keywords
ligands
amidophosphinites
phosphinites
catalytic reactions
palladium
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/EP2013/054583
Other languages
English (en)
French (fr)
Other versions
WO2013135552A2 (de
Inventor
Matthias Beller
Helfried Neumann
Xiao-Feng Wu
Renat Kadyrov
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.)
Evonik Industries AG
Original Assignee
Evonik Industries AG
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 Evonik Industries AG filed Critical Evonik Industries AG
Publication of WO2013135552A2 publication Critical patent/WO2013135552A2/de
Publication of WO2013135552A3 publication Critical patent/WO2013135552A3/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • B01J31/188—Amide derivatives thereof
    • 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
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • 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
    • B01J2531/824—Palladium

Landscapes

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

Abstract

Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von aromatischen und heteroaromatischen Aldehyden durch Umsetzung von Halogen-substituierten Aromaten oder Heteroaromaten mit CO und H2 in Gegenwart eines Palladiumkatalysators, wobei die Umsetzung in Gegenwart einer Base, einer Palladiumverbindung und Phosphinit- oder Amidophosphinitliganden stattfindet. Weiterhin betrifft die Erfindung neue Amidophosphinite sowie Palladiumkatalysatoren, die durch Umsetzung einer Palladiumverbindung mit Phosphinit- oder Amidophosphinitliganden hergestellt werden.
PCT/EP2013/054583 2012-03-13 2013-03-07 Phosphinite und amidophosphinite als liganden in katalytischen reaktionen Ceased WO2013135552A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12159240.6 2012-03-13
EP12159240 2012-03-13

Publications (2)

Publication Number Publication Date
WO2013135552A2 WO2013135552A2 (de) 2013-09-19
WO2013135552A3 true WO2013135552A3 (de) 2014-05-01

Family

ID=47844310

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/054583 Ceased WO2013135552A2 (de) 2012-03-13 2013-03-07 Phosphinite und amidophosphinite als liganden in katalytischen reaktionen

Country Status (1)

Country Link
WO (1) WO2013135552A2 (de)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005014822A1 (de) * 2005-03-30 2006-10-05 Degussa Ag Verfahren zur Herstellung aromatischer Aldehyde

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960932A (en) 1974-10-10 1976-06-01 The University Of Delaware Process for the preparation of aldehydes from organic halides
JPH10330307A (ja) 1997-05-27 1998-12-15 Tosoh Corp 芳香族アルデヒド類の製造方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005014822A1 (de) * 2005-03-30 2006-10-05 Degussa Ag Verfahren zur Herstellung aromatischer Aldehyde

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
AKIHITO IIDA ET AL: "Asymmetric Grignard cross-coupling reaction using chiral ligands derived from carbohydrates.", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 61, no. 7, 1 January 1988 (1988-01-01), pages 2365 - 2367, XP055036920, ISSN: 0009-2673, DOI: 10.1246/bcsj.61.2365 *
ANNA M. TRZECIAK ET AL: "Palladium Chemistry Related to Benzyl Bromide Carbonylation: Mechanistic Studies", MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY, vol. 131, no. 12, 13 December 2000 (2000-12-13), pages 1281 - 1291, XP055036961, ISSN: 0026-9247, DOI: 10.1007/s007060070007 *
KOSTAS I D ET AL: "A palladium complex with a new hemilabile amino- and sulfur-containing phosphinite ligand as an efficient catalyst for the Heck reaction of aryl bromides with styrene. The effect of the amino group", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 59, no. 19, 5 May 2003 (2003-05-05), pages 3467 - 3473, XP004421787, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(03)00474-5 *
NAZAROV A A ET AL: "Synthesis of ferrocenylglucose phosphonite and bisphosphinite: Pd(II) and Pt(II) complexes, Pd-catalyzed allylic alkylation", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 58, no. 42, 14 October 2002 (2002-10-14), pages 8489 - 8492, XP004388259, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(02)01027-X *
TRZECIAK A M ET AL: "STRUCTURAL STUDIES OF PDCL2L2 COMPLEXES WITH FLUORINATED PHOSPHINES, PHOSPHITES, AND PHOSPHINITES AS PRECURSORS OF BENZYL BROMIDE CARBONYLATION CATALYSTS, AND X-RAY CRYSTAL STRUCTURE OF CIS-PDCL2[PPH2(OET)]2", CANADIAN JOURNAL OF CHEMISTRY, NRC RESEARCH PRESS, CA, vol. 79, no. 5/06, 1 January 2001 (2001-01-01), pages 752 - 759, XP001027391, ISSN: 0008-4042, DOI: 10.1139/CJC-79-5-6-752 *

Also Published As

Publication number Publication date
WO2013135552A2 (de) 2013-09-19

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