Diversity-oriented synthesis of multi substituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-pyridyldimethyl(vinyl) silane as a versatile platform for olefin synthesis

被引：181

作者：

Itami, K ^{[1
]}

Nokami, T ^{[1
]}

Ishimura, Y ^{[1
]}

Mitsudo, K ^{[1
]}

Kamei, T ^{[1
]}

Yoshida, J ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synth Chem & Biol Chem, Kyoto 6068501, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2001年 / 123卷 / 47期

关键词：

D O I：

10.1021/ja016790+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel strategy for the diversity-oriented synthesis of multisubstituted olefins, where 2-pyridyldimethyl(vinyl)silane functions as a versatile platform for olefin synthesis, is described. The palladium-catalyzed Heck-type coupling of 2-pyridyldimethyl(vinyl)silanes with organic iodides took place in the presence of Pd-2(dba)(3)/tri-2-furylphosphine catalyst to give beta -substituted vinylsilanes in excellent yields. The Heck-type coupling occurred even with alpha- and beta -substituted 2-pyridyldimethyl(vinyl)silanes. The one-pot double Heck coupling of 2-pyridyldimethyl(vinyl)silane took place with two different aryl iodides to afford beta,beta -diarylated vinylsilanes in good yields. The palladium-catalyzed Hiyama-type coupling of 2-pyridyidimethyl(vinyl)silane with organic halides took place in the presence of tetrabutylammonium fluoride to give di- and trisubstituted olefins in high yields. The sequential integration of Heck-type (or double Heck) coupling and Hiyama-type coupling produced the multisubstituted olefins in regioselective, stereoselective, and diversity-oriented fashions. Especially, the one-pot sequential Heck/Hiyama coupling reaction provides an extremely facile entry into a diverse range of stereodefined multisubstituted olefins. Mechanistic considerations of both Heck-type and Hiyama-type coupling reactions are also described.

引用

页码：11577 / 11585

页数：9

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