Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation |
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Authors: | Chen Bo Hou Xue-Long Li Yu-Xue Wu Yun-Dong |
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Affiliation: | Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China. |
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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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