Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes

Molecules

Partha P. Choudhury²  Mark E. Welker¹ 

[1] Department of Chemistry, Wake Forest University, P. O. Box 7486, Winston-Salem, NC 27109, USA; E-Mail

关键词: organosilanes;    1;    3-dienes;    enyne metathesis;    Diels-Alder;    cross coupling;   

DOI  :  10.3390/molecules200916892

来源: mdpi

【 摘 要 】

2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.