Catalytic Alcoholysis of Tetramethylsilane via Pt-Mediated C−H Bond Activation

Heyduk, Alan F. and Labinger, Jay A. and Bercaw, John E. (2003) Catalytic Alcoholysis of Tetramethylsilane via Pt-Mediated C−H Bond Activation. Journal of the American Chemical Society, 125 (21). pp. 6366-6367. ISSN 0002-7863. doi:10.1021/ja029099v. https://resolver.caltech.edu/CaltechAUTHORS:20170417-065654691

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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, Me_3SiOCH_2CF_3, 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.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja029099v	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja029099v	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ja029099v	Publisher	Supporting Information

ORCID:

Author	ORCID
Labinger, Jay A.	0000-0002-1942-9232

Additional Information:

© 2003 American Chemical Society. Received 25 October 2002. Published online 6 May 2003. Published in print 1 May 2003. We thank Mike Sailor (UCSD) and T. Don Tilley (UCB) for helpful recommendations, and we are grateful to NIH (CA94589 to A.F.H.) and BP for financial support.

Funders:

Funding Agency	Grant Number
NIH	CA94589
BP	UNSPECIFIED

Issue or Number:

DOI:

10.1021/ja029099v

Record Number:

CaltechAUTHORS:20170417-065654691

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20170417-065654691

Official Citation:

Catalytic Alcoholysis of Tetramethylsilane via Pt-Mediated C−H Bond Activation Alan F. Heyduk, Jay A. Labinger, and John E. Bercaw Journal of the American Chemical Society 2003 125 (21), 6366-6367 DOI: 10.1021/ja029099v

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ID Code:

76583

Collection:

CaltechAUTHORS

Deposited By:

Ruth Sustaita

Deposited On:

17 Apr 2017 17:32

Last Modified:

15 Nov 2021 17:01

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