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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

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
› Author AffiliationsWe 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.

Key words

C–H activation - cobalt - N-chlorobenzamide - annulation - room temperature

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1794-1314.
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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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