Categories: C-Si Bond Formation > Silanes
Synthesis of alkynylsilanes
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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 quaternary ammonium pivalate catalyzes a metal-free C-silylation protocol
of terminal alkynes with commercially available N,O-bis(silyl)acetamides
as silylating agents. The reaction proceeds under mild conditions and tolerates
a range of functionalities.
A. Bannykh, P. M. Pihko, Org. Lett., 2024,
26, 1991-1995.
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.
A hydrogen atom transfer (HAT) strategy in combination with
visible-light-driven photocatalysis achieves a direct coupling reaction between
benzene sulfonyl acetylene and silanes. An alkynylation of hydrosilanes in the
presence of reactive groups was achieved with this strategy.
X. Li, F. Zhang, Y. Zhong, N. Li, J. Xu, B. Fan, J. Org. Chem., 2023, 88,
11675-11682.