Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane.
[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).
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
Kenichiro
K
Itami
Yousuke
Y
Ushiogi
Toshiki
T
Nokami
Youichi
Y
Ohashi
Jun-ichi
J
Yoshida