Chemoselective one-pot cleavage and oxidation of silyl ethers to corresponding carbonyl compounds using IBX and acid catalysts

Herein, we describe the chemoselective one-pot cleavage and oxidation of silyl ethers using catalytic amount of TsOH<middle dot>H2O and IBX in DMSO. The oxidation of primary alkyl TBS ethers afforded the corresponding aldehydes in 51-94% yields, in the presence of aryl TBS, MOM, and PMB ethers, as well as N-Boc and acetonide groups. Secondary benzyl TBS ethers bearing aryl TBS ethers were also oxidized to ketones in moderate yields. A possible reaction pathway was also proposed. The chemoselective one-pot cleavage and oxidation of alkyl silyl ethers using TsOH<middle dot>H2O and IBX in DMSOafforded the corresponding carbonyl compounds in 46-94% yields, in the presence of aryl TBS and MOMethers, as well as N-Boc and acetonide groups.