Synthesis 2022; 54(14): 3289-3297
DOI: 10.1055/a-1794-1314
paper

Cobalt(III)-Catalyzed C–H Activation/Annulation Cascade Reaction of N-Chlorobenzamides with 2-Acetylenic Ketones at Room Temperature

Authors

  • Zhouping Wu

    a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China
  • Qinwen Zheng

    b   State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. of China
  • Guanghui Lv

    c   Department of Pharmacy, Taihe Hospital, Hubei University of Medicine, No. 32 South Renmin Road, Shiyan, Huibei 442000, P. R. of China
  • Ruizhi Lai

    a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China
  • Yao Hu

    a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China
  • Li Hai

    a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China
  • Yong Wu

    a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. of China

We are grateful for the support from Sichuan Science and Technology Program (No: 2020YJ0221; 2018JY0537).


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Abstract

A mild cascade annulation of Co(III)-catalyzed N-chlorobenz­amides with 2-acetylenic ketones at room temperature is reported. This reaction sets N–Cl bond of N-chlorobenzamide as an internal oxidant, displaying broad functional group tolerance and excellent reverse selectivity of alkyne insertion under mild and safe conditions. The cascade reaction offers a straightforward and mild protocol to construct isoquinolones in high yields at room temperature.

Supporting Information



Publication History

Received: 25 February 2022

Accepted after revision: 10 March 2022

Accepted Manuscript online:
10 March 2022

Article published online:
03 May 2022

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