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Alkali Metal-Hydroxide-Catalyzed C(sp)-H Bond silylation

Anton A. Toutov, Kerry N. Betz, David P. Schuman, Wen-Bo Liu, Alexey Fedorov , Brian M. Stoltz* and Robert H. Grubbs*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: stoltzcaltech.edu, rhgcaltech.edu

A. A. Toutov, K. N. Betz, D. P. Schuman, W.-B. Liu, A. Fedorov, B. M. Stoltz, R. H. Grubbs, J. Am. Chem. Soc., 2017, 139, 1668-1674.

DOI: 10.1021/jacs.6b12114


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Abstract

NaOH and KOH catalyze a mild, scalable, and chemoselective catalytic cross-dehydrogenative C-H bond functionalization protocol for the construction of C(sp)-Si bonds in a single step. The scope of the alkyne and hydrosilane partners is substantial, providing an entry point into various organosilane building blocks.

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Key Words

alkynylsilanes


ID: J48-Y2017