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WO2011113925A3 - Carbonylation of organic zinc compounds - Google Patents

Carbonylation of organic zinc compounds Download PDF

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Publication number
WO2011113925A3
WO2011113925A3 PCT/EP2011/054104 EP2011054104W WO2011113925A3 WO 2011113925 A3 WO2011113925 A3 WO 2011113925A3 EP 2011054104 W EP2011054104 W EP 2011054104W WO 2011113925 A3 WO2011113925 A3 WO 2011113925A3
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
carbonylation
zinc compounds
organic zinc
zn
Prior art date
Application number
PCT/EP2011/054104
Other languages
German (de)
French (fr)
Other versions
WO2011113925A2 (en
Inventor
Paul Knochel
Sebastian Bernhardt
Albrecht Metzger
Original Assignee
Ludwig-Maximilians-Universität München
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
Priority to DE102010003015.5 priority Critical
Priority to DE102010003015A priority patent/DE102010003015A1/en
Application filed by Ludwig-Maximilians-Universität München filed Critical Ludwig-Maximilians-Universität München
Publication of WO2011113925A2 publication Critical patent/WO2011113925A2/en
Publication of WO2011113925A3 publication Critical patent/WO2011113925A3/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/122Metal aryl or alkyl compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B49/00Grignard reactions
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/30Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/18Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28Radicals substituted by singly-bound oxygen or sulfur atoms
    • C07D213/30Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D261/00Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00Compounds containing elements of Groups 2 or 12 of the Periodic System
    • C07F3/06Zinc compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32Addition reactions to C=C or C-C triple bonds
    • B01J2231/321Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/02Systems containing only non-condensed rings with a three-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring

Abstract

The invention relates to methods for producing organic compounds comprising at least one functional group, in particular carboxylic acids, alcohols, esters, amides, ketones, aldehydes or amines, and to compounds for the production thereof, to uses and to the production of such compounds. The compounds used are compounds of formula (Ia) or (Ib): R-Zn-X⋅MgX2⋅LiCl, (Ia); R1R2-Zn⋅2MgX2⋅2LiCl, (Ib), where R, R1 and R2 are organic groups and X is a halide.
PCT/EP2011/054104 2010-03-18 2011-03-18 Carbonylation of organic zinc compounds WO2011113925A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE102010003015.5 2010-03-18
DE102010003015A DE102010003015A1 (en) 2010-03-18 2010-03-18 Carbonylation of organic zinc compounds

Publications (2)

Publication Number Publication Date
WO2011113925A2 WO2011113925A2 (en) 2011-09-22
WO2011113925A3 true WO2011113925A3 (en) 2011-12-01

Family

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PCT/EP2011/054104 WO2011113925A2 (en) 2010-03-18 2011-03-18 Carbonylation of organic zinc compounds

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DE (1) DE102010003015A1 (en)
WO (1) WO2011113925A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2746259A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746260A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
CN106518655B (en) * 2016-09-08 2019-01-04 山东理工大学 A method of sheet ibuprofen crystal being prepared from aqueous solution by adding crystal control agent

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4981995A (en) * 1987-03-20 1991-01-01 Varadaraj Elango Method for producing ibuprofen
DE102007022490A1 (en) * 2007-05-14 2008-11-20 Ludwig-Maximilians-Universität Bisamide-zinc bases

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4990681A (en) 1989-12-04 1991-02-05 Curtis Thomas A Method for removing hydrogen fluoride from mixtures comprising aromatic ketones

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4981995A (en) * 1987-03-20 1991-01-01 Varadaraj Elango Method for producing ibuprofen
DE102007022490A1 (en) * 2007-05-14 2008-11-20 Ludwig-Maximilians-Universität Bisamide-zinc bases

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
ALBRECHT METZGER ET AL: "Polyfunctional benzylic zinc chlorides by the direct insertion of magnesium into benzylic chlorides in the presence of LiCl and ZnCl2", CHEMICAL COMMUNICATIONS, no. 44, 1 January 2008 (2008-01-01), pages 5824, XP055007488, ISSN: 1359-7345, DOI: 10.1039/b812396a *
ARKADY KRASOVSKIY ET AL: "Soluble Lanthanide Salts (LnCl3.2 LiCl) for the Improved Addition of Organomagnesium Reagents to Carbonyl Compounds", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 45, no. 3, 9 January 2006 (2006-01-09), pages 497 - 500, XP055007492, ISSN: 1433-7851, DOI: 10.1002/anie.200502485 *
CHARLES S. YEUNG ET AL: "Beyond Aresta's Complex: Ni- and Pd-Catalyzed Organozinc Coupling with CO 2", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 130, no. 25, 1 June 2008 (2008-06-01), pages 7826 - 7827, XP055007465, ISSN: 0002-7863, DOI: 10.1021/ja803435w *
FABIAN M. PILLER ET AL: "Convenient Preparation of Polyfunctional Aryl Magnesium Reagents by a Direct Magnesium Insertion in the Presence of LiCl", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 47, no. 36, 25 August 2008 (2008-08-25), pages 6802 - 6806, XP055007491, ISSN: 1433-7851, DOI: 10.1002/anie.200801968 *
HIDENORI OCHIAI ET AL: "Nickel-Catalyzed Carboxylation of Organozinc Reagents with CO 2", ORGANIC LETTERS, vol. 10, no. 13, 1 July 2008 (2008-07-01), pages 2681 - 2683, XP055007466, ISSN: 1523-7060, DOI: 10.1021/ol800764u *
KOJI KOBAYASHI ET AL: "Transition-Metal-Free Carboxylation of Organozinc Reagents Using CO 2 in DMF Solvent", ORGANIC LETTERS, vol. 11, no. 9, 7 May 2009 (2009-05-07), pages 2035 - 2037, XP055007463, ISSN: 1523-7060, DOI: 10.1021/ol900528h *
MOSRIN MARC ET AL: "High temperature zincation of functionalized aromatics and heteroaromatics using TMPZnCl.cntdot.LiCl and microwave irradiation", CHEMICAL COMMUNICATIONS - CHEMCOM; [6015D], ROYAL SOCIETY OF CHEMISTRY, GB, no. 37, 1 August 2009 (2009-08-01), pages 5615 - 1617, XP009131218, ISSN: 1359-7345, DOI: 10.1039/B913693B *

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Publication number Publication date
WO2011113925A2 (en) 2011-09-22
DE102010003015A1 (en) 2011-11-17

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