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,* Chihiro Nakamaki, Katsuhiro Shimono, Michael Schelper, Takuya Kurahashi, and Tamejiro Hiyama
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
J. Am. Chem. Soc., 2005, 127 (36), pp 12506–12507
DOI: 10.1021/ja054484g
Publication Date (Web): August 17, 2005
Copyright © 2005 American Chemical Society
*

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

, shimizu@npc05.kuic.kyoto-u.ac.jp

Abstract

Abstract Image

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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History

  • Published In Issue September 14, 2005
  • Received July 7, 2005

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