Reductive Deprotection of Silyl Groups with Wilkinson's Catalyst/Catechol Borane.

Traditionally silyl groups are deprotected with acids and fluorides. These methods are, however, less discriminating when multi-silyl groups are present in the same molecule resulting in lower yields of desired products. The manipulation of these functions during the total synthesis of natural products, e.g. prostaglandins and isoprostanes, requires the selective protection and deprotection of these groups.We are reporting here on a mild, selective and efficient method for the reductive deprotection of silyl groups using Wilkinson's catalyst/catechol borane or catechol borane alone.