Direct Carbon-Carbon σ Bond Amination of Unstrained Arylalkylketones

Authors：Hu, Xinwei; Shao, Youxiang; Xie, Haisheng^*; Chen, Xin; Chen, Fengjuan; Ke, Zhuofeng^*; Jiang, Huanfeng; Zeng, Wei^*

Source：ACS Catalysis, 2020, 10(15): 8402-8408.

DOI：10.1021/acscatal.0c02683

• rhodium catalysis
• amination
• indoles
• C-C bond activation

Described herein is the development of an unprecedented approach to direct amination of unstrained arylketone Csp(2)-Csp(2) sigma bonds with sulfonylazides via Rh(III)catalyzed Csp(2)-Csp(2) 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.

• Institution
  中山大学