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Diamination/Oxidative Cross-Coupling/Bicyclization of Anilines and Methyl Ketones: Direct I2-Promoted Synthesis of 1,2-Fused Oxindoles

Author:
Zhang, Jingjing, Wu, Xia, Gao, Qinghe, Geng, Xiao, Zhao, Peng, Wu, Yan-Dong, Wu, Anxin
Source:
Organic letters 2017 v.19 no.2 pp. 408-411
ISSN:
1523-7052
Subject:
carbon-hydrogen bond activation, chemical structure, cross-coupling reactions, indoles, ketones
Abstract:
An I₂-promoted domino bicyclization approach via multiple sequential C–H functionalization was serendipitously discovered for the synthesis of 1,2-fused oxindoles from methyl ketones and anilines. This approach was optimized, resulting in a concise and atom-economical approach for the one-pot construction of 1,2-fused oxindoles from methyl ketones and anilines rather than using preexisting indolin-3-ones or indoles. Mechanistic studies revealed that the key step involved an oxidative cross-coupling between in situ generated phenylglyoxal and α,α-diaminoketone.
Agid:
5793281