Organic & Biomolecular Chemistry 2008-06-21

The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide.

Syed Tasadaque A Shah, Patrick J Guiry

Index: Org. Biomol. Chem. 6(12) , 2168-72, (2008)

Full Text: HTML

Abstract

An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities of TMSBr.