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

A copper-catalyzed oxidative cleavage reaction of alkynes using NFSI and TBHP was described. Various terminal and internal alkyne substrates were employed to render quick access to aryl ketone products in moderate to good yields. NFSI not only functioned as N-centered radical precursors but also eng...

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Bibliographic Details
Published in:Organic letters Vol. 22; no. 21; pp. 8618 - 8623
Main Authors: Tang, Lin, Yang, Fang, Cheng, Hao, Tan, Chen, Jin, Chaochao, Chen, Hanfei, Huang, Yifan, Zhang, Shuaifei, Song, Weihan, Tan, Jiajing
Format: Journal Article
Language:English
Published: American Chemical Society 06-11-2020
Online Access:Get full text
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Summary:A copper-catalyzed oxidative cleavage reaction of alkynes using NFSI and TBHP was described. Various terminal and internal alkyne substrates were employed to render quick access to aryl ketone products in moderate to good yields. NFSI not only functioned as N-centered radical precursors but also engaged in the aryl group migration. Mechanistic studies also suggested the important role of water in the title reactions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03201