3 years ago

Co(III)-Catalyzed Coupling-Cyclization of Aryl C–H Bonds with α-Diazoketones Involving Wolff Rearrangement

Co(III)-Catalyzed Coupling-Cyclization of Aryl C–H
Bonds with α-Diazoketones Involving Wolff Rearrangement
Wei Zeng, Youxiang Shao, Xinwei Hu, Zhuofeng Ke, Yuanfu Deng, Huanfeng Jiang, Haisheng Xie, Xun Chen
An unusual cobalt(III)-catalyzed cross-coupling/cyclization of aryl C–H bonds of N-nitrosoanilines with α-diazo-β-ketoesters has been achieved. This protocol features a unique combination of Csp2-H activation/Wolff rearrangement process, allowing for the rapid assembly of quaternary 2-oxindoles. The empirical evidence and density functional theory (DFT) calculations reveal the trapping process of transient acceptor ketene intermediates by cobalt metallocycles.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b03668

DOI: 10.1021/acscatal.7b03668

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