Selective Silylation of Alcohols, Phenols and Oximes Using N‐Chlorosaccharin as an Efficient Catalyst under Mild and Solvent‐Free Conditions

Abstract

Efficient silylation of OH group in alcohols, phenols and oximes is described using a catalytic amount of N-chlorosaccharin and hexamethyldisilazane (HMDS) under mild and solvent-free conditions. This silylation reaction can be carried out with excellent and interesting various selectivities.

Recent advances in catalytic silylation of hydroxyl‐bearing compounds: A green technique for protection of alcohols using Si–O bond formations

“…Over 29 examples of various hydroxylbearing compounds were studied. [164] The silyl ethers were produced using the various primary, secondary, tertiary, benzylic, allylic, and cyclic alcohols as well as phenols and naphtholsethers in excellent yields and in short reaction times. They observed that this method has a good to excellent selectivity for the silylation of primary and secondary aliphatic alcohols despite that of tertiary ones.…”

“…Although the exact mechanism of this conversion is not clear, the authors proposed a mechanism for these reactions, which has been showed in Scheme 47. [164] As shown in Scheme 48, the chlorinated HMDS 1 formation can be assumed from the reaction of HMDS and N-chlorosaccharin as a catalyst containing electrophilic chlorine. Silyl ether and 2 are produced as a result of the treatment of alcohol (or oxime) with 1.…”