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

Zhouping Wu; Qinwen Zheng; Guanghui Lv; Ruizhi Lai; Yao Hu; Li Hai; Yong Wu

doi:10.1055/a-1794-1314

Synthesis, Table of Contents

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

^aKey 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

^bState Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. of China
Guanghui Lv

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

^aKey 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

^aKey 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

^aKey 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∗

^aKey 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

Abstract

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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

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References

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Supplementary Material

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