WO2014083109 PROCESS FOR THE REMOVAL AND RETURN OF A CATALYST TO A LIQUID PHASE MEDIUM AND ITS USE IN CROSS-COUPLING REACTIONS

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Publication Number WO/2014/083109

Publication Date 05.06.2014

International Application No. PCT/EP2013/074974

International Filing Date 28.11.2013

IPC

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CPC

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Applicants

PHOSPHONICS LTD [GB]/[GB]
MURRAY, Paul [IE]/[GB]

Inventors

MURRAY, Paul
WILKES, Robin
NORTH, Christopher

Agents

GEARY, Stephen

Priority Data

1221402.9

28.11.2012

Publication Language English (en)

Filing Language English (EN)

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Title

(EN) PROCESS FOR THE REMOVAL AND RETURN OF A CATALYST TO A LIQUID PHASE MEDIUM AND ITS USE IN CROSS-COUPLING REACTIONS

(FR) PROCÉDÉ POUR LE RETRAIT D'UN CATALYSEUR D'UN MILIEU EN PHASE LIQUIDE ET SON RENVOI VERS CELUI-CI

Abstract

(EN) A process for the selective removal of a component from a liquid phase and subsequently returning the component to a liquid phase is disclosed. A novel compound of formula (I) [SUP]-[[L]-[G]]a (I) in which L is a linking group, G is an aryl group having a leaving group LG selected from Cl, Br, I, sulfonate such as triflate, a diazo group, a nitrile, an ester and an alkoxy group and substituent Q is selected from H, NR2, OR, C02R, F, Cl, N02 CN and SUP is a support having a plurality of groups -[L]-[G] bound to the support is contacted with the liquid phase to bind the component to the compound I thereby forming a captured component which is separated from and may be returned to the liquid phase. The compound I is especially useful in binding homogeneous catalysts to remove it from a reaction medium and selectively returning the catalyst to the reaction medium at a later stage. The compound is particularly useful for cross-coupling reactions, for example in Suzuki reactions.

(FR) L'invention porte sur un procédé pour le retrait sélectif d'un constituant d'une phase liquide et par la suite le renvoi du constituant vers une phase liquide. Un nouveau composé de formule (I) [SUP]-[[L]-[G]]_a (I), dans laquelle L représente un groupe de liaison, G représente un groupe aryle portant un groupe partant LG choisi parmi Cl, Br, I, un groupe sulfonate tel qu'un groupe triflate, un groupe diazoïque, un groupe nitrile, un groupe ester et un groupe alcoxy et le substituant Q est choisi parmi H, NR₂, OR, CO₂R, F, Cl, NO₂ et CN et SUP représente un support ayant une pluralité de groupes -[L]-[G] liés au support, est mis en contact avec la phase liquide pour lier le constituant au composé (I), ce qui forme de cette manière un constituant capturé qui est séparé de la phase liquide et peut être renvoyé vers la phase liquide. Le composé (I) est particulièrement utile pour lier des catalyseurs homogènes pour les enlever d'un milieu réactionnel et renvoyer sélectivement le catalyseur vers le milieu réactionnel dans une étape ultérieure. Le composé est particulièrement utile pour des réactions de couplage croisé, par exemple dans des réactions de Suzuki.

B	PERFORMING OPERATIONS; TRANSPORTING
01	PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
J	CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31	Catalysts comprising hydrides, coordination complexes or organic compounds
02	containing organic compounds or metal hydrides
06	containing polymers

B	PERFORMING OPERATIONS; TRANSPORTING
01	PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
J	CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31	Catalysts comprising hydrides, coordination complexes or organic compounds
16	containing coordination complexes

B	PERFORMING OPERATIONS; TRANSPORTING
01	PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
J	CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31	Catalysts comprising hydrides, coordination complexes or organic compounds
16	containing coordination complexes
24	Phosphines

C	CHEMISTRY; METALLURGY
08	ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
G	MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
77	Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon
04	Polysiloxanes
38	Polysiloxanes modified by chemical after-treatment
382	containing atoms other than carbon, hydrogen, oxygen or silicon
385	containing halogens

C	CHEMISTRY; METALLURGY
08	ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
G	MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
77	Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon
04	Polysiloxanes
38	Polysiloxanes modified by chemical after-treatment
382	containing atoms other than carbon, hydrogen, oxygen or silicon
388	containing nitrogen

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1. WO2014083109 - PROCESS FOR THE REMOVAL AND RETURN OF A CATALYST TO A LIQUID PHASE MEDIUM AND ITS USE IN CROSS-COUPLING REACTIONS

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
B	GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
37	Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
04	Substitution

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
F	ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
17	Metallocenes
02	of metals of Groups 8, 9 or 10 of the Periodic System

C	CHEMISTRY; METALLURGY
08	ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
L	COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
83	Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
04	Polysiloxanes

Y	SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
02	TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
P	CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
20	Technologies relating to chemical industry
50	Improvements relating to the production of bulk chemicals

B	PERFORMING OPERATIONS; TRANSPORTING
01	PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
J	CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2231	Catalytic reactions performed with catalysts classified in B01J31/00
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
42	Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
4205	C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
4211	Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group

B	PERFORMING OPERATIONS; TRANSPORTING
01	PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
J	CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2231	Catalytic reactions performed with catalysts classified in B01J31/00
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
42	Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
4205	C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
4211	Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group