CaltechAUTHORS
  A Caltech Library Service

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

[img] PDF - Supplemental Material
See Usage Policy.

62kB

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20170417-065654691

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:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja029099vDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja029099vPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja029099vPublisherSupporting Information
ORCID:
AuthorORCID
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 AgencyGrant Number
NIHCA94589
BPUNSPECIFIED
Issue or Number:21
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
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76583
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:17 Apr 2017 17:32
Last Modified:15 Nov 2021 17:01

Repository Staff Only: item control page