Catalytic alcoholysis of tetramethylsilane via Pt-mediated C-H bond activation

Journal of the American Chemical Society
Alan F HeydukJohn E Bercaw

Abstract

Tetramethylsilane reacts with 2,2,2-trifluoroethanol (TFE) in the presence of a cationic platinum(II) catalyst [(NN)PtMe(TFE)]+ (NN = 1,2-bis(3,5-dimethylphenylimino)butane). Catalytic Si-C bond heterolysis results in the formation of the trimethylsilyl ether, Me3SiOCH2CF3, accompanied by liberation of one equivalent of methane. Preliminary experiments suggest that a rate-determining C-H bond activation precedes rapid attack by solvent at silicon to yield the silyl ether product and regenerate the active platinum methyl cation.

References

May 31, 2002·Nature·Jay A Labinger, John E Bercaw
Sep 4, 1998·Angewandte Chemie·Shannon S StahlJohn E Bercaw

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Citations

Sep 17, 2011·Journal of the American Chemical Society·Mengmeng Yu, Xuefeng Fu
Nov 7, 2012·Journal of the American Chemical Society·Masahiro OnoeNaoto Chatani
Dec 4, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Shu-Bin ZhaoSuning Wang
Aug 22, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Hongwei XuWesley H Bernskoetter
Nov 10, 2013·Chemical Communications : Chem Comm·Matthias MüllerHolger F Bettinger
Jan 31, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Hajime KameoHiroshi Nakazawa
Aug 16, 2013·Beilstein Journal of Organic Chemistry·Manuel A OrtuñoAgustí Lledós
Feb 14, 2009·Organic Letters·Wangqing KongShengming Ma
Jun 9, 2005·Chemical Reviews·Martin Lersch, Mats Tilset
Feb 18, 2010·Organometallics·D Luke Nelsen, Michel R Gagné

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