Suzuki-miyaura cross-coupling of 1, 1-dichloro-1-alkenes with 9-alkyl-9-BBN

…, C Fosse, A Pernolet, E Roulland

Index: Liron, Frederic; Fosse, Celine; Pernolet, Alban; Roulland, Emmanuel Journal of Organic Chemistry, 2007 , vol. 72, # 6 p. 2220 - 2223

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Citation Number: 40

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 ...