Traditionally, water is not a popular solvent for organic reactions. The limited solubility of many organic substrates and reagents as well as the fact that a variety of functional groups is reactive toward water have traditionally contributed to this lack of popularity of water as a reaction medium. Contrarily, the chemistry of all life processes occurs in aqueous media, and few people will doubt the high quality and efficiency of these transformations!
Recently there has been a revival of interest in water as the reaction medium in organic chemistry. Our increasing concern for the environment and for safe chemical procedures are reasons for this change in attitude. Interestingly, many organic reactions (and particularly carbon-carbon bond formation reactions) are accelerated in water relative to organic solvents. Water may also have a favorable effect on the stereochemistry of a variety of organic transformations.1,2 And finally, very recent studies by Shapless et al. (vide infra) have shown that limited aqueous solubility can be turned into an advantage!
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