Palladium-catalyzed carbene insertion and trapping with carbon nucleophiles

Organic Letters
Sean K J Devine, David L Van Vranken

Abstract

Palladium catalysts are shown to catalyze the three-component coupling of vinyl halides, trimethylsilyldiazomethane, and stabilized carbon nucleophiles. The reaction is believed to proceed through a palladium-carbene intermediate LX(R)PdCHSiMe 3 that undergoes migration of the vinyl substituent to the electrophilic carbene center to generate an eta 3-allylpalladium intermediate. The allylpalladium intermediate is attacked by the carbon nucleophile to generate a vinylsilane product.

References

Oct 2, 2003·Chemical Communications : Chem Comm·Martin BröringSascha Stellwag
Apr 20, 2007·Organic Letters·Sean K J Devine, David L Van Vranken
Jun 26, 2007·Journal of the American Chemical Society·Cheng PengJianbo Wang
Jan 12, 2008·Journal of the American Chemical Society·Cheng PengJianbo Wang

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Citations

Feb 24, 2010·Chemical Communications : Chem Comm·Xia ZhaoJianbo Wang
Dec 1, 2015·Organic Letters·Hua ZhaoHongbin Zhai
Oct 4, 2014·Organic Letters·Eugene S GutmanDavid L Van Vranken
Jan 22, 2010·Angewandte Chemie·Zhenhua ZhangJianbo Wang
Apr 27, 2010·Chemical Society Reviews·Erica JellemaBas de Bruin
Jul 26, 2011·Chemical Society Reviews·Zhihui Shao, Hongbin Zhang
Sep 24, 2013·Chemical Communications : Chem Comm·Yu-Ying YeYong-Min Liang
May 23, 2012·Chemistry : a European Journal·Isabel MeanaPablo Espinet
Apr 30, 2014·Organic & Biomolecular Chemistry·Fangdong HuJianbo Wang
Mar 14, 2013·Chemical Communications : Chem Comm·Ping-Xin ZhouYong-Min Liang
Dec 5, 2012·Chemical Communications : Chem Comm·Ping-Xin ZhouYong-Min Liang
Sep 15, 2010·Journal of the American Chemical Society·Lei ZhouJianbo Wang
Sep 4, 2014·Chemical Reviews·Chang-Liang Sun, Zhang-Jie Shi
May 2, 2020·Organic Letters·Guillaume PisellaJerome Waser
Mar 5, 2011·Journal of the American Chemical Society·Zhenhua ZhangJianbo Wang
May 23, 2020·Journal of the American Chemical Society·Ying Xia, Jianbo Wang

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