A Facile Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Silicon and Tin via Palladium-Catalyzed Cross-Coupling Reaction

Ming-Zhong Cai; Zhou Zhou; Ping-Ping Wang

doi:10.1055/s-2006-926341

PAPER

A Facile Stereoselective Synthesis of Difunctionalized 1,3-Dienes Containing Silicon and Tin via Palladium-Catalyzed Cross-Coupling Reaction

Ming-Zhong Cai*^a, Zhou Zhou^a, Ping-Ping Wang^b
^a School of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027, P. R. of China
Fax: +86(791)8517500; e-Mail: caimzhong@163.com;
^b Department of Chemistry, Jiujiang College, Jiujiang 332000, P. R. of China

Abstract

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Abstract

Hydromagnesiation of alkynylsilanes 1 in diethyl ether gave (Z)-α-silylvinyl Grignard reagents 2, which underwent a cross-coupling reaction with (E)-α-iodovinylstannanes 3 in the presence of Pd(PPh₃)₄ catalyst to afford stereoselectively the difunctionalized 1,3-dienes 4 containing silicon and tin in good yields.

Key words

hydromagnesiation - (E)-α-iodovinylstannane - difunctionalized 1,3-diene - cross-coupling reaction - palladium catalysis - stereoselective synthesis

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