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Transition‐Metal‐Free C3 Arylation of Indoles with Aryl Halides
Author(s) -
Chen Ji,
Wu Jimmy
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612311
Subject(s) - chemistry , aryl , regioselectivity , aryne , halide , transition metal , electron transfer , photochemistry , electron paramagnetic resonance , isotopic labeling , combinatorial chemistry , radical , organic chemistry , catalysis , alkyl , physics , nuclear magnetic resonance
We report an unprecedented transition metal‐free coupling of indoles with aryl halides. The reaction is promoted by KOtBu and is regioselective for C3 over N. The use of degassed solvents devoid of oxygen is necessary for the success of the transformation. Preliminary studies implicate a hybrid mechanism that involves both aryne intermediates and non‐propagative radical processes. Electron transfer is also a distinct possibility. These conclusions were substantiated by EPR data, isotopic labeling studies, and the use of radical scavengers and electron transfer inhibitors.