Abstract

A variety of TBDMS ethers were directly transprotected into their acetates/benzoates with acetyl chloride/ benzoyl chloride in a one-pot procedure using CuBr2 (30 mol%). Chemo-selective transprotection of aliphatic TBDMS ethers in the presence of aromatic TBDMS ethers was achieved using 10 mol% of the catalyst. Various sensitive functional groups such as ketals, ketones, alkenes, allyl and benzyl ethers were found to be compatible under the reaction conditions.

Keywords: TBDMS ethers, copper(II) bromide, transprotection, acetates, benzoates, chemoselectivity