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A Copper-Catalyzed Aerobic [1,3]-Nitrogen Shift through Nitrogen-Radical 4-exo-trig Cyclization
Angewandte Chemie International Edition 56(48):15436-15440 Nov 2017

Li, Yan; Wang, Rui; Wang, Tao; Cheng, Xiu-Fen; Zhou, Xin; Fei, Fan; Wang, Xi-Sheng

A novel radical [1,3]-nitrogen shift catalyzed by copper diacetate under 1 atm of oxygen atmosphere for the construction of a diversity of indole structure motifs from α,α-disubstituted benzylamine has been developed, in which oxygen was used as a clean terminal oxidant and water was produced as the only byproduct. Of particular note is five inert bonds were cleaved, and two C-N bonds and one C-C double bond were constructed in one pot during this transformation. This unique method demonstrated broad application prospect for late-stage modification of biologically active natural products and drugs. Mechanistic investigations indicate that a unique 4-exo-trig cyclization of an aminyl radical to phenyl ring was involved in the catalytic cycle.

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