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One-Pot Synthesis of Trisubstituted Conjugated Dienes via Sequential Suzuki-Miyaura Cross-Coupling with Alkenyl- and Alkyltrifluoroborates

Gary A. Molander and Yasuo Yokoyama*

*Department of Chemistry, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan, Email: yasuo-ysophia.ac.jp

G. A. Molander, Y. Yokoyama, J. Org. Chem., 2006, 71, 2493-2498.

DOI: 10.1021/jo052636k (free Supporting Information)


Abstract

A sequential, palladium-catalyzed, stereoselective disubstitution of 1,1-dibromoalkenes with various alkenyltrifluoroborates followed by alkyltrifluoroborates proceeds smoothly in one pot under mild reaction conditions to provide the corresponding trisubstituted, conjugated dienes in excellent yield.

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Key Words

Dienes, Suzuki Coupling, Trifluoroborates


ID: J42-Y2006-770