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

Partha P Choudhury; Mark E Welker

doi:10.3390/molecules200916892

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

Molecules. 2015 Sep 16;20(9):16892-907. doi: 10.3390/molecules200916892.

Authors

Partha P Choudhury¹, Mark E Welker²

Affiliations

¹ Department of Chemistry, Wake Forest University, P. O. Box 7486, Winston-Salem, NC 27109, USA. pchoudhury@gru.edu.
² Department of Chemistry, Wake Forest University, P. O. Box 7486, Winston-Salem, NC 27109, USA. welker@wfu.edu.

Abstract

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.

Keywords: 1,3-dienes; Diels-Alder; cross coupling; enyne metathesis; organosilanes.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkenes / chemistry*
Catalysis
Cycloaddition Reaction
Molecular Structure
Silicon / chemistry*
Stereoisomerism

Substances

Alkenes
Silicon