Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation

Bo Chen, Xue Long Hou, Yu Xue Li, Yun Dong Wu

Research output: Contribution to journalArticlepeer-review

177 Scopus citations

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 CuIII-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.

Original languageEnglish (US)
Pages (from-to)7668-7671
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number20
DOIs
StatePublished - May 25 2011

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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