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Title: Lewis Acidity of Bis(perfluorocatecholato)silane: Aldehyde Hydrosilylation Catalyzed by a Neutral Silicon Compound

Abstract

Bis(perfluorocatecholato)silane Si(cat(F)2 was prepared, and stoichiometric binding to Lewis bases was demonstrated with fluoride, triethylphosphine oxide, and N,N'-diisopropylbenzamide. The potent Lewis acidity of Si(cat(F)2 was suggested from catalytic hydrosilylation and silylcyanation reactions with aldehydes. Mechanistic studies of hydrosilylation using an optically active silane substrate, R-(+)-methyl-(1-naphthyl)phenylsilane, proceeded with predominant stereochemical retention at silicon, consistent with a carbonyl activation pathway. The enantiospecificity was dependent on solvent and salt effects, with increasing solvent polarity or addition of NBu4BAr(F)4 leading to a diminished enantiomeric ratio. The medium effects are consistent with an ionic mechanism, wherein hydride transfer occurs prior to silicon-oxygen bond formation.

Authors:
 [1];  [1];  [1]
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  1. Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Research Org.:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1257852
Grant/Contract Number:  
AC02-05CH11231; CHE-0841786; S10-RR027172
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 137; Journal Issue: 16; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Liberman-Martin, Allegra L., Bergman, Robert G., and Tilley, T. Don. Lewis Acidity of Bis(perfluorocatecholato)silane: Aldehyde Hydrosilylation Catalyzed by a Neutral Silicon Compound. United States: N. p., 2015. Web. doi:10.1021/jacs.5b02807.
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Liberman-Martin, Allegra L., Bergman, Robert G., & Tilley, T. Don. Lewis Acidity of Bis(perfluorocatecholato)silane: Aldehyde Hydrosilylation Catalyzed by a Neutral Silicon Compound. United States. https://doi.org/10.1021/jacs.5b02807
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Liberman-Martin, Allegra L., Bergman, Robert G., and Tilley, T. Don. Thu . "Lewis Acidity of Bis(perfluorocatecholato)silane: Aldehyde Hydrosilylation Catalyzed by a Neutral Silicon Compound". United States. https://doi.org/10.1021/jacs.5b02807. https://www.osti.gov/servlets/purl/1257852.
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@article{osti_1257852,
title = {Lewis Acidity of Bis(perfluorocatecholato)silane: Aldehyde Hydrosilylation Catalyzed by a Neutral Silicon Compound},
author = {Liberman-Martin, Allegra L. and Bergman, Robert G. and Tilley, T. Don},
abstractNote = {Bis(perfluorocatecholato)silane Si(cat(F)2 was prepared, and stoichiometric binding to Lewis bases was demonstrated with fluoride, triethylphosphine oxide, and N,N'-diisopropylbenzamide. The potent Lewis acidity of Si(cat(F)2 was suggested from catalytic hydrosilylation and silylcyanation reactions with aldehydes. Mechanistic studies of hydrosilylation using an optically active silane substrate, R-(+)-methyl-(1-naphthyl)phenylsilane, proceeded with predominant stereochemical retention at silicon, consistent with a carbonyl activation pathway. The enantiospecificity was dependent on solvent and salt effects, with increasing solvent polarity or addition of NBu4BAr(F)4 leading to a diminished enantiomeric ratio. The medium effects are consistent with an ionic mechanism, wherein hydride transfer occurs prior to silicon-oxygen bond formation.},
doi = {10.1021/jacs.5b02807},
journal = {Journal of the American Chemical Society},
number = 16,
volume = 137,
place = {United States},
year = {Thu Apr 16 00:00:00 EDT 2015},
month = {Thu Apr 16 00:00:00 EDT 2015}
}
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https://doi.org/10.1021/jacs.5b02807
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Figures / Tables:

Figure 1. Figure 1.: ORTEP diagram of 2, with thermal elipsoids at 50% probability. Tris(dimethylamino)sulfonium cations are omitted for clarity.
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