TBuOK-Promoted Cyclization of Imines with Aryl Halides

Li, Y.-W.; Zheng, H.-X.; Yang, B.; Shan, X.-H.; Qu, J.-P.; Kang, Y.-B.

Organic Letters 22(11): 4553-4556


ISSN/ISBN: 1523-7052
PMID: 32437166
Accession: 072902232

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A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.