Water plays a crucial role: Small molecule catalyzed C–C/C–X bond forming reactions using organosilicon reagents under “wet” conditions

Abstract

Organocatalytic manipulation of silicon reagents, which enables the efficient formation of carbon–carbon (C–C) or carbon–heteroatom (C–X) bonds have been attracting considerable attention since the past few decades. In several instances, surprisingly, water is a remarkably essential molecule to promote the desired transformation to achieve superb outcomes in terms of reaction rates, chemical yields, and stereoselectivities. From the catalytic amount to solvent quantity, water plays a crucial role in the asymmetric/non-asymmetric catalytic transformations such as aldol reactions, Michael addition reactions, Mannich reactions, α-alkylation reactions, and other related strategies. In the current review, we present a comprehensive report on the recent advances of small molecule catalyzed addition reactions of organosilicon reagents under “wet” condition (46 examples). Examples featuring in the synthesis of complex natural products are also discussed.