Remote C-H bond functionalization reveals the distance-dependent isotope effect

Jiao Jie Li, Ramesh Giri, Jin Quan Yu

Research output: Contribution to journalArticlepeer-review

72 Scopus citations

Abstract

Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage.

Original languageEnglish (US)
Pages (from-to)6979-6987
Number of pages9
JournalTetrahedron
Volume64
Issue number29
DOIs
StatePublished - Jul 14 2008

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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