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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, Email: shimizunpc05.kuic.kyoto-u.ac.jp

M. Shimizu, C. Nakamaki, K. Shimono, M. Schelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc., 2005, 127, 12506-12507.

DOI: 10.1021/ja054484g (free Supporting Information)


Abstract

Palladium-catalyzed cross-coupling reaction of 1,1-diboryl-1-alkenes with aryl and alkenyl iodides proceeded stereoselectively to the corresponding mono-coupled product as a single diastereomer. A subsequent coupling with another aryl iodide afforded various triarylalkenes in their stereochemically pure form.

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Key Words

Suzuki Coupling, Arylation


ID: J48-Y2005-2580