Iron-Catalyzed Oxidative Coupling of Indoline-2-ones with Aminobenzamides via Dual C–H Functionalization

Iron-Catalyzed Oxidative Coupling of Indoline-2-ones with Aminobenzamides via Dual C–H Functionalization

We describe an unprecedented dual C–H functionalization of indolin-2-one via an oxidative C­(sp3)–H/N–H/X–H (X = N, C, S) cross-coupling protocol, which is catalyzed by a simple iron salt under mild and ligand-free conditions and employs air (molecular oxygen) as the terminal oxidant. This method is...

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Bibliographic Details
Published in:Organic letters Vol. 22; no. 10; pp. 3825 - 3829
Main Authors: Lai, Yi-Huan, Wu, Run-Shi, Huang, Jie, Huang, Jun-Yu, Xu, Da-Zhen
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-05-2020
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Summary:We describe an unprecedented dual C–H functionalization of indolin-2-one via an oxidative C­(sp3)–H/N–H/X–H (X = N, C, S) cross-coupling protocol, which is catalyzed by a simple iron salt under mild and ligand-free conditions and employs air (molecular oxygen) as the terminal oxidant. This method is readily applicable for the construction of tetrasubstituted carbon centers from methylenes and provides a wide variety of spiro N-heterocyclic oxindoles.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01066