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

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, Email:

F. Liron, C. Fosse, A. Pernolet, E. Roulland, J. Org. Chem., 2007, 72, 2220-2223.

DOI: 10.1021/jo061908w

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The use of bisphosphine ligands with a large P-Pd-P bite angle allowed to synthesize Z-chlorinated internal alkenes in good yields by a selective Suzuki-Miyaura monocoupling process of 9-alkyl-9-BBN with 1,1-dichloro-1-alkenes. These monochlorinated olefins could be further transformed providing stereospecifically trisubstituted olefins.

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Key Words

Suzuki Coupling, Alkenes, Vinylchlorides

ID: J42-Y2007-0970