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Modular Counter-Fischer-Indole Synthesis through Radical-Enolate Coupling

Hyunho Chung, Jeongyun Kim, Gisela A. González-Montiel, Paul Ha-Yeon Cheong* and Hong Geun Lee*

*Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA; Seoul National University, Seoul 08826, Republic of Korea, Email: cheonghoregonstate.edu, hgleeesnu.ac.kr

H. Chung, J. Kim,. G. A. González-Montiel, P. H.-Y. Cheong, H. G. Lee, Org. Lett., 2021, 23, 1096-1102.

DOI: 10.1021/acs.orglett.1c00003 (free Supporting Information)


Abstract

A single-electron transfer mediates a modular indole formation from a 2-iodoaniline derivative and a ketone. This transition-metal-free reaction offers a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated.

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Key Words

indoles


ID: J54-Y2021