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Water profoundly affects many organic reactions by accelerating them or changing their selectivity. Performing reactions "on-water" offers an intriguing opportunity to influence chemical reactivity. A nebulizer plume is an efficient… Click to show full abstract
Water profoundly affects many organic reactions by accelerating them or changing their selectivity. Performing reactions "on-water" offers an intriguing opportunity to influence chemical reactivity. A nebulizer plume is an efficient way of generating microdroplets-the uniquely complex reaction environment which opens alternative possibilities that are not readily accessible in bulk emulsions. We describe the on-water switch of chemoselectivity in the formation of triazoles controlled by the on-water environment in dual spray. These conditions facilitate elimination of H-SO2F from the triazoline intermediate, whereas the reaction in organic solvents results in the exclusive HBr elimination. The influence of two-phase conditions was investigated to obtain the best reaction efficiency, and the crucial importance of the water/organic interface interactions was verified by pH variation and D2O use.
Journal Title: Journal of the American Chemical Society
Year Published: 2021
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