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

• DOI: 10.1021/acscatal.7b03668
• Publication Date: 2018-01-16T15:41:49Z
• Authors: Xinwei Hu; Xun Chen; Youxiang Shao; Haisheng Xie; Yuanfu Deng; Zhuofeng Ke; Huanfeng Jiang; Wei Zeng
• Keywords: Wolff rearrangement

An unusual cobalt(III)-catalyzed cross-coupling/cyclization of aryl C–H bonds N-nitrosoanilines with α-diazo-β-ketoesters has been achieved. This protocol features a unique combination Csp2-H activation/Wolff rearrangement process, allowing for the rapid assembly quaternary 2-oxindoles. The empirical evidence and density functional theory (DFT) calculations reveal trapping process transient acceptor ketene intermediates by cobalt metallocycles.