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Reactions in Water through "On-Water" Mechanism.

Ever-evolving advances in synthetic protocols including water-compatible catalysts have enriched current understanding of sustainable organic chemistry. However, the lack of a clearly defined classification system has led to confusion when referring to chemical processes performed using water without any organic solvents. In this discussion, we propose that reactions should be collectively called to be "in water", as long as operated "in water" when water is used as a reaction medium. When the reactions are accelerated in water as heterogeneous mixtures, they can be regarded as following an "on-water" mechanism . Because the original term "on water" coined by Sharpless is incompatible with the concept of catalyst, on water used in this review covers all the interface involving water where the reactions are accelerated in comparison with the corresponding homogeneous system. As a result of unconcluded dispute on the conventional "on water" model, the modified interface model defines three water layers: water molecules are oriented to extrude protons toward the oil phase in the inner surface, surrounded by a secondary layer, and finally enwrapped by the bulk water layer. Furthermore, catalytic reactions performed in water are categorized in a broad sense into seven types. In the light of the latitudinous outlook on the role of water at the interface, selected examples of reactions especially over the past decade that can give higher yield in 100% water than in organic solvents are herein reviewed to understand the contribution of the water molecules at multifarious interfaces.