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. 2005 Sep 14;127(36):12506-7.
doi: 10.1021/ja054484g.

Stereoselective cross-coupling reaction of 1,1-Diboryl-1-alkenes with electrophiles: a highly stereocontrolled approach to 1,1,2-triaryl-1-alkenes

Masaki Shimizu  1 , Chihiro Nakamaki, Katsuhiro Shimono, Michael Schelper, Takuya Kurahashi, Tamejiro Hiyama
Affiliations

Stereoselective cross-coupling reaction of 1,1-Diboryl-1-alkenes with electrophiles: a highly stereocontrolled approach to 1,1,2-triaryl-1-alkenes

Masaki Shimizu et al. J Am Chem Soc. .

Abstract

Palladium-catalyzed cross-coupling reaction of 1,1-diboryl-1-alkenes with aryl and alkenyl iodides was found to proceed stereoselectively, giving rise to the corresponding mono-coupled product as a single diastereomer with E-configuration. Second coupling of the initial product with another aryl iodide affords diverse triarylalkenes in their stereochemically pure form. This highly stereoselective approach for triarylalkenes allows one to synthesize both diastereomers in one pot from 1,1-diboryl-1-alkenes.

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