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Published November 18, 2016 | Supplemental Material
Journal Article Open

Sodium Hydroxide Catalyzed Dehydrocoupling of Alcohols with Hydrosilanes

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.

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.

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