Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality

Organic Letters
B M TrostZachary T Ball

Abstract

[reaction: see text] Ruthenium-catalyzed alkyne hydrosilylation or silyl-alkyne Alder ene reactions provide entry into benzyldimethylsilyl (BDMS)-substituted alkenes. The BDMS-vinylsilanes are further elaborated through mild palladium-catalyzed cross coupling and show significant stability to intervening synthetic operations, including silyl ether deprotection.

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Citations

Jul 14, 2005·Journal of the American Chemical Society·Barry M TrostKai M Laemmerhold
Dec 15, 2005·Journal of the American Chemical Society·Barry M Trost, Zachary T Ball
May 18, 2006·Journal of the American Chemical Society·Barry M TrostBrian D Faulk
May 10, 2007·Journal of the American Chemical Society·Eun Jin Cho, Daesung Lee
Dec 3, 2010·The Journal of Organic Chemistry·Scott E DenmarkJoseck M Muhuhi
Feb 9, 2010·The Journal of Organic Chemistry·Biao Lu, J R Falck
Jul 17, 2007·Organic Letters·Yun Zhang, James S Panek
Mar 4, 2010·Chemical Communications : Chem Comm·Subramaniyan Mannathan, Chien-Hong Cheng
Aug 28, 2015·Journal of the American Chemical Society·Barry M TrostMing-Yu Ngai
Aug 23, 2016·Journal of the American Chemical Society·Barry M TrostRainer Kalkofen
Nov 5, 2004·Organic Letters·Barry M TrostAndrew E Pomerantz
Mar 18, 2017·Organic & Biomolecular Chemistry·Mohamed A B MostafaAndrew Sutherland
Apr 30, 2017·Chemical Science·Barry M TrostJames J Cregg
Jun 15, 2017·Journal of the American Chemical Society·Matthew R Elsby, Samuel A Johnson
Apr 22, 2015·Chemical Communications : Chem Comm·Hongze LiZhenlei Song
Jun 16, 2018·Angewandte Chemie·Eva Rivera-Chao, Martín Fañanás-Mastral
Oct 26, 2012·Chemistry : a European Journal·Barry M TrostVincent S Chan
Feb 28, 2014·Angewandte Chemie·Stephan M Rummelt, Alois Fürstner
Oct 13, 2011·Chemistry : a European Journal·Christine M BoehnerDavid R Spring
Mar 29, 2014·Chemistry : a European Journal·Sanjay W Chavhan, Matthew J Cook
Dec 3, 2014·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Takashi Ikawa
Nov 1, 2018·Chemical Communications : Chem Comm·Xueyan ZhangShengtao Ding
Mar 6, 2009·Organic & Biomolecular Chemistry·Hannah F SoreDavid R Spring
Jan 1, 2010·European Journal of Organic Chemistry·Holly A ReichardGlenn C Micalizio
Mar 25, 2010·Angewandte Chemie·Scott E Denmark, Jack H-C Liu
Dec 1, 2010·Israel Journal of Chemistry·Scott E Denmark, Jack H-C Liu
Oct 6, 2005·Angewandte Chemie·Barry M TrostMichael T Rudd
Oct 14, 2010·Organic & Biomolecular Chemistry·Hannah F SoreDavid R Spring
Nov 4, 2011·Chemical Society Reviews·Hannah F SoreDavid R Spring
Jun 13, 2019·Chemistry : a European Journal·Lauren E Longobardi, Alois Fürstner
Jun 2, 2020·Chemical & Pharmaceutical Bulletin·Hiromichi Egami
Jul 16, 2020·Chemistry, an Asian Journal·Sonu Yadav, S S V Ramasastry
Mar 26, 2011·Chemical Science·Holly A Reichard, Glenn C Micalizio
Mar 3, 2011·Angewandte Chemie·Géraldine Rousseau, Bernhard Breit
Mar 1, 2012·Chemistry : a European Journal·Julián BergueiroSusana López

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