title: Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation.
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.
authors.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.
authors.forename: Bo
authors.initials: B
authors.lastname: Chen
authors.forename: Xue-Long
authors.initials: XL
authors.lastname: Hou
authors.forename: Yu-Xue
authors.initials: YX
authors.lastname: Li
authors.forename: Yun-Dong
authors.initials: YD
authors.lastname: Wu