WO2012016147A3 - Ligands for selective asymmetric hydroformylation - Google Patents

Ligands for selective asymmetric hydroformylation Download PDF

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Publication number
WO2012016147A3
WO2012016147A3 PCT/US2011/045897 US2011045897W WO2012016147A3 WO 2012016147 A3 WO2012016147 A3 WO 2012016147A3 US 2011045897 W US2011045897 W US 2011045897W WO 2012016147 A3 WO2012016147 A3 WO 2012016147A3
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WO
WIPO (PCT)
Prior art keywords
ligands
asymmetric hydroformylation
selective asymmetric
selective
hydroformylation
Prior art date
Application number
PCT/US2011/045897
Other languages
French (fr)
Other versions
WO2012016147A2 (en
Inventor
Christopher James Cobley
Gary Noonan
Matthew Clarke
Original Assignee
Dr. Reddy's Laboratories Ltd.
Dr. Reddy's Laboratories, 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 Dr. Reddy's Laboratories Ltd., Dr. Reddy's Laboratories, Inc. filed Critical Dr. Reddy's Laboratories Ltd.
Priority to EP11813250.5A priority Critical patent/EP2598510A4/en
Priority to JP2013522001A priority patent/JP2013532691A/en
Publication of WO2012016147A2 publication Critical patent/WO2012016147A2/en
Publication of WO2012016147A3 publication Critical patent/WO2012016147A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C07C45/505—Asymmetric hydroformylation
    • 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
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=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
    • B01J31/24—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
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • 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
    • C07F9/6568—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 atoms as the only ring hetero atoms
    • C07F9/65683—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 atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
    • 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
    • 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
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

In an aspect, the invention provides compounds of the formula 4: wherein the constituent variables are defined herein.
PCT/US2011/045897 2010-07-30 2011-07-29 Ligands for selective asymmetric hydroformylation WO2012016147A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP11813250.5A EP2598510A4 (en) 2010-07-30 2011-07-29 Ligands for selective asymmetric hydroformylation
JP2013522001A JP2013532691A (en) 2010-07-30 2011-07-29 Ligands for selective asymmetric hydroformylation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36923810P 2010-07-30 2010-07-30
US61/369,238 2010-07-30

Publications (2)

Publication Number Publication Date
WO2012016147A2 WO2012016147A2 (en) 2012-02-02
WO2012016147A3 true WO2012016147A3 (en) 2012-04-19

Family

ID=45530741

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/045897 WO2012016147A2 (en) 2010-07-30 2011-07-29 Ligands for selective asymmetric hydroformylation

Country Status (3)

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EP (1) EP2598510A4 (en)
JP (1) JP2013532691A (en)
WO (1) WO2012016147A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104744514B (en) * 2013-12-27 2018-03-23 中国科学院上海药物研究所 A kind of chiral phosphorus alkene part, synthetic method and its application in asymmetric reaction
US9308527B2 (en) 2014-03-17 2016-04-12 Eastman Chemical Company Phosphorous compounds useful as ligands and compositions and methods regarding them
US10144751B1 (en) 2017-11-28 2018-12-04 Eastman Chemical Company Highly isoselective catalyst for alkene hydroformylation
US10183961B1 (en) * 2017-11-28 2019-01-22 Eastman Chemical Company Highly isoselective catalyst for alkene hydroformylation
CA3179702A1 (en) 2020-05-05 2021-11-11 Nuvalent, Inc. Heteroaromatic macrocyclic ether chemotherapeutic agents
CN115916754A (en) 2020-05-05 2023-04-04 纽威伦特公司 Heteroaromatic macrocyclic ether chemotherapeutic agents
EP4204388A1 (en) * 2020-08-25 2023-07-05 Eastman Chemical Company Olefin hydroformylation processes using hydrocarbon solvents and fluorinated solvents in the presence of phospholane-phosphite ligands
CN115989210A (en) * 2020-08-25 2023-04-18 伊士曼化工公司 Phospholane-phosphite ligands for olefin hydroformylation catalysts

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3846020B2 (en) * 1998-04-07 2006-11-15 三菱化学株式会社 Bisphosphite compound and method for producing aldehydes using the compound

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ARENA, C. G. ET AL.: "Structural Control in Palladium(II)-Catalyzed Enantiose lective Allylic Alkylation by New Chiral Phosphine-Phosphite and Pyridine-Phosphite Ligands.", TETRAHEDRON ASYMMETRY, vol. 11, 2000, pages 2765 - 2779, XP004228727 *
FERNANDEZ-PEREZ, H. ET AL.: "Highly Modular P-OP Ligands for Asymmetric Hydrogenation: Synthesis, Catalytic Activity, and Mechanism.", CHEM. EUR. J., vol. 16, 23 April 2010 (2010-04-23), pages 6495 - 6508, XP055083468 *
ROBERT, T. ET AL.: "Asymmetric Hydroformylation Using Taddol-Based Chiral Phosphine-Phosphite Ligands.", ORGANOMETALLICS, vol. 29, 18 December 2009 (2009-12-18), pages 478 - 483, XP055083473 *
See also references of EP2598510A4 *

Also Published As

Publication number Publication date
JP2013532691A (en) 2013-08-19
EP2598510A4 (en) 2014-02-26
WO2012016147A2 (en) 2012-02-02
EP2598510A2 (en) 2013-06-05

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