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WO2005023731A3 - Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome. - Google Patents

Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome. Download PDF

Info

Publication number
WO2005023731A3
WO2005023731A3 PCT/FR2004/002021 FR2004002021W WO2005023731A3 WO 2005023731 A3 WO2005023731 A3 WO 2005023731A3 FR 2004002021 W FR2004002021 W FR 2004002021W WO 2005023731 A3 WO2005023731 A3 WO 2005023731A3
Authority
WO
WIPO (PCT)
Prior art keywords
carbon
forming
leaving group
heteroatom
bond
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/FR2004/002021
Other languages
English (en)
Other versions
WO2005023731A2 (fr
Inventor
Jean-Francis Spindler
Marc Taillefer
Henri-Jean Cristau
Pascal Philippe Cellier
Armelle Ouali
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhodia Chimie SAS
Original Assignee
Rhodia Chimie SAS
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 Rhodia Chimie SAS filed Critical Rhodia Chimie SAS
Priority to US10/568,850 priority Critical patent/US20090240061A1/en
Priority to EP04767803A priority patent/EP1663914A2/fr
Publication of WO2005023731A2 publication Critical patent/WO2005023731A2/fr
Publication of WO2005023731A3 publication Critical patent/WO2005023731A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic 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
    • C07D231/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—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
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • C07B41/04—Formation or introduction of functional groups containing oxygen of ether, acetal or ketal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • 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
    • C07C67/343—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 by increase in the number of carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention a pour objet un procédé de création d'une liaison carbone-carbone ou carbone-hétéroatome par réaction d'un composé insaturé porteur d'un groupe partant et d'un composé nucléophile, en l'absence de ligand. L'invention vise notamment la création de liaison carbone-azote selon un procédé d'arylation de dérivés organiques azotés. Le procédé, selon l'invention, de création d'une liaison carbone-carbone ou carbone-hétéroatome par réaction d'un composé insaturé porteur d'un groupe partant et d'un composé nucléophile apportant un atome de carbone ou un hétéroatome (HE) susceptible de se substituer au groupe partant, créant ainsi une liaison C-C ou C-HE, en présence d'un catalyseur ô base de cuivre et d'une base est caractérisé par le fait que la réaction a lieu en l'absence d'un ligand et dans un solvant de type nitrile.
PCT/FR2004/002021 2003-08-28 2004-07-28 Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome. Ceased WO2005023731A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/568,850 US20090240061A1 (en) 2003-08-28 2004-07-28 Method for forming a carbon-carbon or carbon-heteroatom bond
EP04767803A EP1663914A2 (fr) 2003-08-28 2004-07-28 Procede de formation d une liaison carbone-carbone ou carbon e-heteroatome.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0310253 2003-08-28
FR0310253A FR2859205B1 (fr) 2003-08-28 2003-08-28 Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome

Publications (2)

Publication Number Publication Date
WO2005023731A2 WO2005023731A2 (fr) 2005-03-17
WO2005023731A3 true WO2005023731A3 (fr) 2005-05-12

Family

ID=34130633

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2004/002021 Ceased WO2005023731A2 (fr) 2003-08-28 2004-07-28 Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome.

Country Status (4)

Country Link
US (1) US20090240061A1 (fr)
EP (1) EP1663914A2 (fr)
FR (1) FR2859205B1 (fr)
WO (1) WO2005023731A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9272274B2 (en) 2007-12-06 2016-03-01 Centre National De La Recherche Scientifique (C.N.R.S.) Catalytic system for cross-coupling reactions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9162953B2 (en) 2006-07-05 2015-10-20 Centre Nationale De Recherche Scientifique Iron-copper co-catalyzed process for carbon-carbon or carbon-heteroatom bonding
FR2915200B1 (fr) * 2007-04-20 2009-07-03 Centre Nat Rech Scient Procede de preparation de ligands de type phosphines butadieniques,leurs complexes avec le cuivre,et leurs applications en catalyse

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002085838A1 (fr) * 2001-04-24 2002-10-31 Massachusetts Institute Of Technology Formation par catalyse de cuivre de liaisons carbone-heteroatome et carbone-carbone
WO2003053885A1 (fr) * 2001-12-20 2003-07-03 Rhodia Chimie Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002085838A1 (fr) * 2001-04-24 2002-10-31 Massachusetts Institute Of Technology Formation par catalyse de cuivre de liaisons carbone-heteroatome et carbone-carbone
WO2003053885A1 (fr) * 2001-12-20 2003-07-03 Rhodia Chimie Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome.

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
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 *
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 *
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 *
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 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9272274B2 (en) 2007-12-06 2016-03-01 Centre National De La Recherche Scientifique (C.N.R.S.) Catalytic system for cross-coupling reactions
US9861971B2 (en) 2007-12-06 2018-01-09 Centre National De La Recherche Scientifique (C.N.R.S) Catalytic system for cross-coupling reactions

Also Published As

Publication number Publication date
US20090240061A1 (en) 2009-09-24
FR2859205B1 (fr) 2006-02-03
EP1663914A2 (fr) 2006-06-07
WO2005023731A2 (fr) 2005-03-17
FR2859205A1 (fr) 2005-03-04

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