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