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Sodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes

Anton A. Toutov, Kerry N. Betz, Michael C. Haibach, Andrew M. Romine and Robert H. Grubbs*

*Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email:

A. A. Toutov, K. N. Betz, M. C. Haibach, A. M. Romine, R. H. Grubbs, Org. Lett., 2016, 18, 5776-5779.

DOI: 10.1021/acs.orglett.6b01687 (free Supporting Information)

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Inexpensive NaOH as the catalyst enables a 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.

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Key Words

silyl ethers

ID: J54-Y2016