Affiliation:
1. Institute of Organic Chemistry, Faculty of Chemistry and Pharmacy, University of Regensburg, 93040 Regensburg, Germany.
Abstract
Water can accelerate a variety of organic reactions far beyond the rates observed in classical organic solvents. However, using pure water as a solvent introduces solubility constraints that have limited the applicability of efficient photochemistry in particular. We report here the formation of aggregates between pairs of arenes, heteroarenes, enamines, or esters with different electron affinities in an aqueous medium, leading to an oil-water phase boundary through substrate melting point depression. The active hydrogen atoms in the reactants engage in hydrogen bonds with water, thereby accelerating photochemical reactions. This methodology realizes appealingly simple conditions for aqueous coupling reactions of complex solid molecules, including complex drug molecules that are poorly soluble in water.
Publisher
American Association for the Advancement of Science (AAAS)
Cited by
12 articles.
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