Enzyme-inspired functional surfactant for aerobic oxidation of activated alcohols to aldehydes in water
B.-T. Chen, K.V. Bukhryakov, R. Sougrat, V.O. Rodionov
ACS Catal., 5 (2), 1313-1317, (2015)
Micellar catalysis, oxidation, copper, TEMPO, fluorous surfactant
We describe an enzyme-inspired catalytic system based on a rationally designed multifunctional amphiphile. The resulting micelles feature metal-binding sites and stable free radical moieties as well as fluorous pockets that attract and preconcentrate molecular oxygen. In the presence of copper ions, the micelles effect chemoselective aerobic alcohol oxidation under ambient conditions in water, a transformation that is challenging to achieve nonenzymatically.
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