Categories: C-H Bond Formation >
Desilylations
Recent Literature
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.