Title:
METHOD FOR FORMING A CARBON-CARBON OR CARBON-HETEROATOM BOND
Document Type and Number:
WIPO Patent Application WO2005023731
Kind Code:
A3
Abstract:
The invention relates to a method for forming a carbon-carbon or carbon-heteroatom bond by reacting an unsaturated compound carrying a leaving group and a nucleophilic compound, in the absence of a ligand. The aim of the invention is especially to form carbon-nitrogen bonds according to a method for the arylation of nitrogenated organic derivatives. According to the inventive method, a carbon-carbon or carbon-heteroatom bond is formed by reacting an unsaturated compound carrying a leaving group with a nucleophilic compound donating a carbon atom or a heteroatom (HE) that can substitute the leaving group, thus forming a C-C or C-HE bond, in the presence of a copper-based catalyst and a base. Said metal is characterised in that the reaction takes place in the absence of a ligand and in a nitrile-type solvent.
Inventors:
SPINDLER JEAN-FRANCIS (FR)
TAILLEFER MARC (FR)
CRISTAU HENRI-JEAN (FR)
CELLIER PASCAL PHILIPPE (FR)
OUALI ARMELLE (FR)
TAILLEFER MARC (FR)
CRISTAU HENRI-JEAN (FR)
CELLIER PASCAL PHILIPPE (FR)
OUALI ARMELLE (FR)
Application Number:
PCT/FR2004/002021
Publication Date:
May 12, 2005
Filing Date:
July 28, 2004
Export Citation:
Assignee:
RHODIA CHIMIE SA (FR)
SPINDLER JEAN-FRANCIS (FR)
TAILLEFER MARC (FR)
CRISTAU HENRI-JEAN (FR)
CELLIER PASCAL PHILIPPE (FR)
OUALI ARMELLE (FR)
SPINDLER JEAN-FRANCIS (FR)
TAILLEFER MARC (FR)
CRISTAU HENRI-JEAN (FR)
CELLIER PASCAL PHILIPPE (FR)
OUALI ARMELLE (FR)
International Classes:
C07B37/04; C07B41/04; C07B41/08; C07B41/12; C07B43/06; C07C41/16; C07C67/04; C07C67/343; C07D231/12; (IPC1-7): C07B37/04; C07B43/06; C07D231/12
Domestic Patent References:
| WO2003053885A1 | 2003-07-03 | |||
| WO2002085838A1 | 2002-10-31 |
Other References:
KANG S-K ET AL: "COPPER-CATALYZED N-ARYLATION OF ARYL IODIDES WITH BENZAMIDES OR NITROGEN HETEROCYLCES IN THE PRESENCE OF ETHYLENEDIAMINE", SYNLETT, THIEME VERLAG, STUTTGART, DE, vol. 3, 4 March 2002 (2002-03-04), pages 427 - 430, XP001156275, ISSN: 0936-5214
HENNESSY ET AL: "A general and mild copper-catalyzed arylation of diethyl malonate", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 4, no. 2, 2002, pages 269 - 272, XP002245231, ISSN: 1523-7060
HE H ET AL: "Synthesis of diaryl ethers through the copper-catalyzed arylation of phenols with aryl halides using microwave heating", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 17, 21 April 2003 (2003-04-21), pages 3445 - 3446, XP004417829, ISSN: 0040-4039
HE H ET AL: "Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 16, 14 April 2003 (2003-04-14), pages 3385 - 3386, XP004417082, ISSN: 0040-4039
HENNESSY ET AL: "A general and mild copper-catalyzed arylation of diethyl malonate", ORGANIC LETTERS, ACS, WASHINGTON, DC, US, vol. 4, no. 2, 2002, pages 269 - 272, XP002245231, ISSN: 1523-7060
HE H ET AL: "Synthesis of diaryl ethers through the copper-catalyzed arylation of phenols with aryl halides using microwave heating", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 17, 21 April 2003 (2003-04-21), pages 3445 - 3446, XP004417829, ISSN: 0040-4039
HE H ET AL: "Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 44, no. 16, 14 April 2003 (2003-04-14), pages 3385 - 3386, XP004417082, ISSN: 0040-4039
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