Categories: C-H Bond Formation >
Low loadings of KOTMS catalyze an additive-free, C-, N-, O-, and S-Si bond cleavage of various organosilanes under mild conditions. The novel catalyst system exhibits high efficiency and good functional group compatibility, providing the corresponding products in good to excellent yields.
W. Yao, R. Li, H. Jiang, D. Han, J. Org. Chem., 2018, 83, 2250-2255.
With either 1.0 or even 0.1 equivalents of DBU, smooth desilylation of various terminal acetylenic TMS groups was accomplished selectively in the presence of alkyl silyl ethers and other base-labile groups. Furthermore, more sterically hindered terminal acetylenic silyl groups such as TBDMS and TIPS remained intact under these conditions.
C.-E. Yeom, M. J. Kim, W. Choi, B. M. Kim, Synlett, 2008, 565-568.
A procedure for protiodesilylation of 1-(trimethylsilyl)-1-alkynes involves the use of catalytic amounts of AgNO3. The mechanism and selectivity of this reaction are discussed.
A. Carpita, L. Mannocci, R. Rossi, Eur. J. Org. Chem., 2005, 1367-1377.
L. Zani, S. Alesi, P. G. Cozzi, C. Bolm, J. Org. Chem., 2006, 71, 1558-1562.
Optically active cis-cyclopropane carboxylates can be prepared via a Rh2(S-PTAD)4-catalyzed cyclopropanation of α-silyl styrenes with aryl diazoacetates followed by desilylation of the resulting silyl cyclopropane carboxylates.
Y. Su, Q.-F. Li, Y.-M. Zhao, P. Gu, Org. Lett., 2016, 18, 4356-4359.