Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C–H Bond Arylation
2011; American Chemical Society; Volume: 133; Issue: 20 Linguagem: Inglês
10.1021/ja201425e
ISSN1943-2984
AutoresBo Chen, Xue-Long Hou, Yu-Xue Li, Yun-Dong Wu,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoDFT 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.
Referência(s)