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Sodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes

Toutov, Anton A. and Betz, Kerry N. and Haibach, Michael C. and Romine, Andrew M. and Grubbs, Robert H. (2016) Sodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes. Organic Letters, 18 (22). pp. 5776-5779. ISSN 1523-7060. http://resolver.caltech.edu/CaltechAUTHORS:20161114-093917870

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Abstract

An O–Si bond construction protocol employing abundantly available and inexpensive NaOH as the catalyst is described. The method enables the cross-dehydrogenative coupling of an alcohol and hydrosilane to directly generate the corresponding silyl ether under mild conditions and without the production of stoichiometric salt byproducts. The scope of both coupling partners is excellent, positioning the method for use in complex molecule and materials science applications. A novel Si-based cross-coupling reagent is also reported.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/acs.orglett.6b01687DOIArticle
http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b01687PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.orglett.6b01687PublisherSupporting Information
ORCID:
AuthorORCID
Toutov, Anton A.0000-0002-6561-0462
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2016 American Chemical Society. Received: June 10, 2016; Revised: October 11, 2016; Publication Date (Web): November 9, 2016. This work was supported by the NSF under the CCI Center for Selective C–H Functionalization (CHE-1205646) and under CHE-1212767. A.A.T. is grateful to the Resnick Sustainability Institute at Caltech and to Dow Chemical for a predoctoral fellowship and to NSERC for a PGS D fellowship. We thank S. Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. M. Shahgoli and N. Torian (Caltech) are acknowledged for assistance with high-resolution mass spectrometry. The authors declare no competing financial interest.
Group:Resnick Sustainability Institute
Funders:
Funding AgencyGrant Number
NSFCHE-1205646
NSFCHE-1212767
Resnick Sustainability InstituteUNSPECIFIED
Dow Chemical CompanyUNSPECIFIED
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Record Number:CaltechAUTHORS:20161114-093917870
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20161114-093917870
Official Citation:Sodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes Anton A. Toutov, Kerry N. Betz, Michael C. Haibach, Andrew M. Romine, and Robert H. Grubbs Organic Letters 2016 18 (22), 5776-5779 DOI: 10.1021/acs.orglett.6b01687
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:71983
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:15 Nov 2016 23:54
Last Modified:07 Dec 2016 22:03

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