Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane

Kenichiro Itami; Yousuke Ushiogi; Toshiki Nokami; Youichi Ohashi; Jun-ichi Yoshida

doi:10.1021/ol048620i

Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane

Org Lett. 2004 Oct 14;6(21):3695-8. doi: 10.1021/ol048620i.

Authors

Kenichiro Itami¹, Yousuke Ushiogi, Toshiki Nokami, Youichi Ohashi, Jun-ichi Yoshida

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan. itami@sbchem.kyoto-u.ac.jp

PMID: 15469326
DOI: 10.1021/ol048620i

Abstract

[reaction: see text] We have developed the homocoupling reaction of alkenyl(2-pyridyl)silanes mediated by CuI and CsF, in which the strong directing effect of the 2-pyridyl group was observed. The homocoupling reaction was successfully integrated with the Mizoroki-Heck reaction of vinyl(2-pyridyl)silane with aryl halides, enabling a rapid and stereoselective synthesis of multisubstituted butadienes. From a relatively small compound library, it was possible to detect a number of fluorescent butadienes with a wide range of fluorescence color variations (blue to reddish-orange).