Organic reactions in aqueous media - with a focus on carbon-carbon bond formation

Abstract

Carbon-carbon bond formation is the essence of organic synthesis. Although the well-known Kolbe synthesis was discovered in 1849Ia (the first observation wasmadein 1834byFaraday),'bformorethanacentury, carbon-carbon bond formation in aqueous media has been limited mainly to electrochemical processes and aldol condensation reactions. This is in contrast to the many enzymatic processes that by necessity must occur in an aqueous environment. In the last decade, there has been increasing recognition that organic reactions carried out in aqueous media may offer advantages over those occurring in organic solvents. For example, protection and deprotection processes in organic synthesis can possibly be simplified. This review will survey this area, concentrating mainly on the last decade. The review is organized into three main portions: nonorganometallic reactions, organometallic reactions, and transition-metal-catalyzed organic reactions in aqueous media. The conventional aldol-type and related reactions, stabilized carbanion alkylation reactions, electrochemical reactions as well as bioorganic reactions involving aqueous media and leading to carbon-carbon bond formation will not be included.