Categories: C-Si Bond Formation > Silanes
Synthesis of alkynylsilanes
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.
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.
A rapid and high-yielding silylation of terminal alkynes employing TMSOTf and catalytic quantities of Zn(OTf)2 works well for a variety of substrates including reactive esters.
R. J. Rahaim, Jr., J. T. Shaw, J. Org. Chem., 2008, 73, 2912-2915.
Various alkynylsilanes were efficiently prepared via zinc halides-mediated direct silylation of terminal alkynes with aminosilanes. Base- and nucleophile-sensitive functionalities were tolerated under the reaction conditions. The electrophilic character of this transformation is supported by initial mechanistic studies.
A. A. Andreev, V. V. Konshin, N. V. Komarov, M. Rubin, C. Brouwer, V. Gevorgyan, Org. Lett., 2004, 6, 421-424.