Cleavage of silyl ethers

Protecting Groups

t-Butyldimethylsilyl ethers

Recent Literature

Various tert-butyldimethylsilyl (TBS, TBDMS) ethers as well as tert-butyldiphenylsilyl (TBDPS) ethers can be easily deprotected by employing a catalytic amount of acetyl chloride in dry MeOH in good yields. This mild and convenient method tolerates various other protecting groups and does not lead to acylated or chlorinated byproducts.
A. T. Khan, E. Mondal, Synlett, 2003, 694-698.

A very mild and environmentally benign method for the removal of silyl protecting groups using catalytic amounts of iron in MeOH is particularly effective for cleaving triethylsilyl (TES) groups.
Y.-Q. Yang, J.-R. Cui, L.-G, Zhu, Y.-P. Sun, Y. Wu, Synlett, 2006, 1260-1262.

PMA supported on SiO₂ is found to be an efficient catalyst for the chemoselective, mild deprotection of TBDMS ethers. Various labile functional groups such as isopropylidene acetal, OTBDPS, OTHP, Oallyl, OBn, alkene, alkyne, OAc, OBz, N-Boc, N-Cbz, N-Fmoc, mesylate, and azide are tolerated. The supported catalyst and the solvent can be readily recovered and recycled.
G.D. K. Kumar, S. Baskaran, J. Org. Chem., 2005, 70, 4520-4523.

With either 1.0 or 0.10 equivalent of DBU, smooth desilylation of various aryl silyl ethers was accomplished selectively in the presence of base-sensitive groups such esters and alkyl silyl ethers. A direct transformation of aryl silyl ethers into biaryl ethers was possible through tandem desilylation and S_NAr reaction with activated aryl fluorides.
C.-E. Yeom, H. W. Kim, S. Y. Lee, B. M. Kim, Synlett, 2007, 146-150.