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

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 m...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-03, Vol.72 (6), p.2220-2223
Main Authors: Liron, Frédéric, Fosse, Céline, Pernolet, Alban, Roulland, Emmanuel
Format: Article
Language:English
Subjects:
Chemical Sciences
Chemistry
Exact sciences and technology
Organic chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo061908w