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

J. Am. Chem. Soc.,
2017, 139 (4), pp 1668–1674; DOI: 10.1021/jacs.6b12114


Disclosed is 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 and additionally enabling the discovery of a number of novel synthetic strategies. Remarkably, the optimal catalysts are NaOH and KOH.