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Direct Carbon–Carbon σ Bond Amination of Unstrained Arylalkylketones

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posted on 2020-07-17, 13:35 authored by Xinwei Hu, Youxiang Shao, Haisheng Xie, Xin Chen, Fengjuan Chen, Zhuofeng Ke, Huanfeng Jiang, Wei Zeng
Described herein is the development of an unprecedented approach to direct amination of unstrained aryl-ketone Csp2–Csp2 sigma bonds with sulfonylazides via Rh­(III)-catalyzed Csp2–Csp2 cleavage. This methodology provides an efficient strategy for acyl groups/amino groups switch at the C2-position of indoles in a straightforward fashion. The combination of experimental and computational studies indicates that beta-aryl elimination derived from enole-based cyclorhodiumates is a key step, while the formation of rhodum nitrene is the rate-limiting process.