Janine Cossy - Grignard Reagents and Transition Metal Catalysts.

Janine Cossy (Ed.)

Grignard Reagents and Transition Metal Catalysts

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Author

Prof. Janine Cossy

Laboratoire de Chimie Organique

Institute of Chemistry, Biology and Innovation (CBI)

UMR 8231

ESPCI ParisTech/CNRS/PSL Research University

10 rue Vauquelin

75231 Paris Cedex 05

France

Janine.Cossy@espci.fr

ISBN 978-3-11-035266-5

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e-ISBN (EPUB) 978-3-11-038343-0

Set-ISBN 978-3-11-035273-3

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Cover image: von Fotograv. - Generalstabens Litografiska Anstalt Stockholm [Public domain], via

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Grard Cahiez

Institut de Recherche de Chimie Paris

CNRS Chimie ParisTech, PSL Research

University

11 rue Pierre et Marie Curie

75005 Paris

France

Catherine S. J. Cazin

EaStCHEM School of Chemistry

University of St Andrews

Purdie Building

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St Andrews

Fife, KY16 9ST

UK

Janine Cossy

Laboratoire de Chimie Organique

Institute of Chemistry, Biology and Innovation (CBI)

UMR CNRS 8231

ESPCI ParisTech/CNRS/PSL Research University

10 rue Vauquelin

75231 Paris Cedex 05

France

Fabienne Fache

Universit Lyon 1

ICBMS UMR CNRS 5246

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Bruno Figadre

CNRS

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Corinne Gosmini

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Ecole Polytechnique

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Normandie Universit

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Alban Moyeux

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Olivier Piva

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Alice Rrat

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Marc Taillefer

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Since the early 1900s, Victor Grignard had been of great impact in organic chemistry in developing organomagnesium reagents called Grignard reagents and, due to the importance of his work, he was awarded the Nobel Prize in 1912. Grignard reagents are often written as RMgX (R = organic part, X= halide), and these reagents can take various forms in both solution and solid states. In solution, they become a mixture of RMg (called organomagnesium reagents) and MgX coming from a redistribution of the ligand in RMgX.

In their education and training, almost all the chemists have had an experience of preparing and/or utilizing Grignard reagents. Grignard reagents are prepared from readily available organo halides and magnesium and more recently i PrMgX.LiCl, called the Turbo Grignard, was used to prepare Grignard reagents from halides by a magnesiumhalide exchange. The Grignard reagents are mainly used to synthesize alcohols from carbonyl derivatives but, one major drawback of the Grignard reagents is that they are not functional group tolerant. However, since the discovery of the reactivity of the Grignard reagents, their reactivity has been modified by the addition of transition metal complexes in the reaction media. It has been reported for the first time by Kharash et al ., around 1940, that CC bonds can be formed by a cross-coupling reaction between a halide and a Grignard reagent catalyzed by metallic halides. Thirty years later in their early work and independly, Kochi, Kumada and Tamao as well as Corriu reported coupling reactions between organo halides and Grignard reagents catalyzed by palladium, nickel and iron salts. Since then a number of reports have been published to realize coupling reactions using, palladium, nickel, iron, cobalt, manganese, copper, silver and to a less extend titanium, chromium, rhodium, ruthenium, etc. showing that the reactivity of Grignard can be modified in the presence of metallic complexes, making them very chemoselective.