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Molecules 2015, 20(9), 16892-16907; doi:10.3390/molecules200916892

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

Department of Chemistry, Wake Forest University, P. O. Box 7486, Winston-Salem, NC 27109, USA
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Author to whom correspondence should be addressed.
Academic Editor: Georgios C. Vougioukalakis
Received: 17 August 2015 / Revised: 7 September 2015 / Accepted: 8 September 2015 / Published: 16 September 2015
(This article belongs to the Special Issue Olefin Metathesis)
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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. View Full-Text
Keywords: organosilanes; 1,3-dienes; enyne metathesis; Diels-Alder; cross coupling organosilanes; 1,3-dienes; enyne metathesis; Diels-Alder; cross coupling
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Choudhury, P.P.; Welker, M.E. Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes. Molecules 2015, 20, 16892-16907.

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