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Suzuki−Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl-9-BBN

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Frédéric Liron,^† Céline Fosse,^‡ Alban Pernolet,^§ and Emmanuel Roulland*^†

Institut de Chimie des Substances Naturelles, CNRS, avenue de la Terrasse, 91198 Gif-sur-Yvette, France, Service de Spectromtrie de Masse, Ecole Normale Suprieure, 24, rue Lhomond, 75231 Paris, Cedex 05, and UMR 7573, Ecole Normale Suprieure de Chimie de Paris, 11, rue Pierre et Marie Curie, 75231, Paris cedex 05, France emmanuel.roulland@icsn.cnrs-gif.fr

J. Org. Chem., 2007, 72 (6), pp 2220–2223

DOI: 10.1021/jo061908w

Publication Date (Web): February 21, 2007

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In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

We addressed an unexplored application of the Suzuki−Miyaura protocol to the cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl-9-BBN. The use of bisphosphine ligands with a large P−Pd−P bite angle allowed us to synthesize Z-chlorinated internal alkenes in good yields resulting from a selective monocoupling process, a recurrent challenge with 1,1-dichloro-1-alkenes. Moreover, these monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.

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Published In Issue March 16, 2007
Received September 15, 2006

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Suzuki−Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl-9-BBN

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Secondary Alkyl Halides at Room Temperature

Boronic Acids: New Coupling Partners in Room-Temperature Suzuki Reactions of Alkyl Bromides. Crystallographic Characterization of an Oxidative-Addition Adduct Generated under Remarkably Mild Conditions

Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates

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