WO2020109217A3 - Ruthenium and osmium cyclic alkyl amino carbene complexes - Google Patents

Ruthenium and osmium cyclic alkyl amino carbene complexes Download PDF

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Publication number
WO2020109217A3
WO2020109217A3 PCT/EP2019/082393 EP2019082393W WO2020109217A3 WO 2020109217 A3 WO2020109217 A3 WO 2020109217A3 EP 2019082393 W EP2019082393 W EP 2019082393W WO 2020109217 A3 WO2020109217 A3 WO 2020109217A3
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WO
WIPO (PCT)
Prior art keywords
cyclic alkyl
alkyl amino
compounds
osmium
ruthenium
Prior art date
Application number
PCT/EP2019/082393
Other languages
French (fr)
Other versions
WO2020109217A2 (en
Inventor
Adam M. Johns
Richard L. Pederson
Doina Gabriela ENE
Ralf Karch
Angelino Doppiu
Original Assignee
Umicore Ag & Co. Kg
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 Umicore Ag & Co. Kg filed Critical Umicore Ag & Co. Kg
Publication of WO2020109217A2 publication Critical patent/WO2020109217A2/en
Publication of WO2020109217A3 publication Critical patent/WO2020109217A3/en

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    • 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • 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)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • 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
    • 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
    • B01J2531/825—Osmium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

Abstract

This invention relates generally to olefin metathesis catalysts comprising cyclic alkyl amino carbenes, to the preparation of such compounds, compositions comprising such compounds, methods of using such compounds, and the use of such compounds in the metathesis of olefins. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and in industrial applications such as oil and gas, fine chemicals and pharmaceuticals.
PCT/EP2019/082393 2018-11-29 2019-11-25 Metal organic compounds WO2020109217A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201862772630P 2018-11-29 2018-11-29
US62/772,630 2018-11-29

Publications (2)

Publication Number Publication Date
WO2020109217A2 WO2020109217A2 (en) 2020-06-04
WO2020109217A3 true WO2020109217A3 (en) 2020-07-09

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PCT/EP2019/082393 WO2020109217A2 (en) 2018-11-29 2019-11-25 Metal organic compounds

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Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3936511A1 (en) * 2020-07-08 2022-01-12 Centre national de la recherche scientifique Ruthenium complexes, their optically pure enantiomers and uses thereof
PL434983A1 (en) 2020-08-17 2022-02-21 Apeiron Synthesis Spółka Akcyjna New ruthenium complexes, methods of their preparation and their application in the cross olefin metathesis reaction
EP4180421A1 (en) * 2021-11-16 2023-05-17 Ecole Nationale Supérieure de Chimie de Rennes Iminium salts with a barralene ring, corresponding ruthenium complexes, and uses thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100022789A1 (en) * 2008-07-25 2010-01-28 Rhodia Operations Catalytic compositions for the metathesis of unsaturated fatty bodies with olefins and metathesis methods using catalytic compositions
WO2014004089A1 (en) * 2012-06-28 2014-01-03 Exxonmobil Chemical Patents Inc. Metathesis catalyst and process for use thereof
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
WO2017055945A1 (en) * 2015-09-30 2017-04-06 Apeiron Synthesis S.A. Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis
WO2017185324A1 (en) * 2016-04-29 2017-11-02 Xia, Ling Group 8 transition metal catalysts and method for making same and process for use of same in olefin disproportionation reactions
WO2019158485A1 (en) * 2018-02-13 2019-08-22 Umicore Ag & Co. Kg Reactions of olefin derivatives in the presence of metathesis catalysts

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100022789A1 (en) * 2008-07-25 2010-01-28 Rhodia Operations Catalytic compositions for the metathesis of unsaturated fatty bodies with olefins and metathesis methods using catalytic compositions
WO2014004089A1 (en) * 2012-06-28 2014-01-03 Exxonmobil Chemical Patents Inc. Metathesis catalyst and process for use thereof
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
WO2017055945A1 (en) * 2015-09-30 2017-04-06 Apeiron Synthesis S.A. Process for producing ruthenium complexes and intermediates thereof and their use in olefin metathesis
WO2017185324A1 (en) * 2016-04-29 2017-11-02 Xia, Ling Group 8 transition metal catalysts and method for making same and process for use of same in olefin disproportionation reactions
WO2019158485A1 (en) * 2018-02-13 2019-08-22 Umicore Ag & Co. Kg Reactions of olefin derivatives in the presence of metathesis catalysts

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CORY M. WEINSTEIN ET AL: "Highly Ambiphilic Room Temperature Stable Six-Membered Cyclic (Alkyl)(amino)carbenes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 140, no. 29, 29 June 2018 (2018-06-29), US, pages 9255 - 9260, XP055695093, ISSN: 0002-7863, DOI: 10.1021/jacs.8b05518 *
EDER TOMÁS-MENDIVIL ET AL: "Bicyclic (Alkyl)(amino)carbenes (BICAACs): Stable Carbenes More Ambiphilic than CAACs", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 139, no. 23, 25 May 2017 (2017-05-25), US, pages 7753 - 7756, XP055695084, ISSN: 0002-7863, DOI: 10.1021/jacs.7b04640 *
ILLYA ROZENBERG ET AL: "Synthesis and Catalytic Properties of Sulfur-Chelated Ruthenium Benzylidenes Bearing a Cyclic (Alkyl)(amino)carbene Ligand", ACS CATALYSIS, vol. 8, no. 9, 6 August 2018 (2018-08-06), US, pages 8182 - 8191, XP055696171, ISSN: 2155-5435, DOI: 10.1021/acscatal.8b02122 *
RAFAL GAWIN ET AL: "Bis(Cyclic Alkyl Amino Carbene) Ruthenium Complexes: A Versatile, Highly Efficient Tool for Olefin Metathesis", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 56, no. 4, 12 December 2016 (2016-12-12), DE, pages 981 - 986, XP055444856, ISSN: 1433-7851, DOI: 10.1002/anie.201609009 *
RAFAL GAWIN ET AL: "Cyclic Alkyl Amino Ruthenium Complexes-Efficient Catalysts for Macrocyclization and Acrylonitrile Cross Metathesis", ACS CATALYSIS, vol. 7, no. 8, 5 July 2017 (2017-07-05), US, pages 5443 - 5449, XP055444858, ISSN: 2155-5435, DOI: 10.1021/acscatal.7b00597 *

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