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Updated: Jun 2, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation
Bo Chen1, Xue-Long Hou, Yu-Xue Li
1Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China.
Abstract:
DFT calculations suggest that the unexpected meta product in the copper-catalyzed arylation of anilide is formed via a Heck-like four-membered-ring transition state involving a Cu(III)-Ph species. A competitive electrophilic substitution mechanism delivers the ortho product when a methoxy group is present at the meta position of pivanilide. A series of experiments including kinetic studies support the involvement of a Cu(I) catalyst.
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