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.
Visible-light irradiation mediates the synthesis of alkynylsilanes in very good yields from alkynes and silanes in the presence of CuCl as precatalyst. A large scale flow reaction and late-stage functionalization of natural products show the potential of the transformation.
Q.-C. Gan, Z.-Q. Song, C.-H. Tung, L.-Z. Wu, Org. Lett., 2022, 24, 5192-5196.
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.