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Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones

Lin Tang, Fang Yang, Hao Cheng, Chen Tan, Chaochao Jin, Hanfei Chen, Yifan Huang, Shuaifei Zhang, Weihan Song and Jiajing Tan*

*Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology (BUCT), Beijing 100029, China, Email:

L. Tang, F. Yang, H. Cheng, C. Tan, C. Jin, H. Chen, Y. Huang, S. Zhang, S. Zhang, W. Song, J. Tan, Org. Lett., 2020, 22, 8618-8623.

DOI: 10.1021/acs.orglett.0c03201

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A copper-catalyzed oxidative cleavage reaction of terminal and internal alkynes using NFSI and TBHP provides aryl ketone products in good yields. NFSI not only functioned as N-centered radical precursor but also engaged in the aryl group migration. Mechanistic studies also suggested the important role of water.

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proposed mechanism

Key Words

aryl ketones, hydrolysis, NFSI, THP

ID: J54-Y2020