Our laboratory found that hot water could efficiently promote ring-opening of epoxides and aziridines by hetero-atom nucleophiles, N-Boc deprotection, Friedel-Crafts alkylation between arenes and epoxides, SN1 direct substitution reactions of allylic and benzylic alcohols, 1,n-isomeration of allylic alcohols, hydroarylation reactions between alkynoates and arenes, and Nazarov reaction.We also found that the combinatory use of these hot water-promoted reactions can lead to the one-pot synthesis of the core structure of complicated natural products without additional catalyst. Instead of a hydrogen-bonding activation mechanism, we suggested that hot water acted as a mild Br�nsted acid/base catalyst in the reactions. The potential influence of the thermal activation, the high ionizing power of water, the concentration of the organic substrates in the hot water-accelerated reactions were also studied to understand the catalytic function of water.

Hot water promoted organic reactions

245th National Meeting (2013)

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