Dual role of carboxylic acid additive: Mechanistic studies and implication for the asymmetric C-H amidation Dedicated to Professor Yoshiaki Nakao on his receipt of the Tetrahedron Young Investigator Award

Donghyeon Gwon, Sehoon Park, Sukbok Chang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

Abstract

Acid additive effects in the Ir-catalyzed C-H amidation of arylphosphoryl compounds were examined. Structure of catalytically active metal species was elucidated: mono-cationic iridium catalyst [CpIr(III)(OAc)](NTf2) being mainly responsible for the C-H bond activation. Mechanistic studies revealed a dual role of carboxylic acid additive operating both in the generation of an iridacyclic intermediate and in the protodemetalation process to release amidated products. The fact that asymmetric C-H amidation was achieved albeit in moderate enantioselectivity by using chiral carboxylic acid supports our proposal especially with regard to the role of acid additive.

Original languageEnglish
Pages (from-to)4504-4511
Number of pages8
JournalTetrahedron
Volume71
Issue number26-27
DOIs
StatePublished - 30 May 2015
Externally publishedYes

Keywords

  • Acid additive effects
  • Asymmetric induction
  • C-H amidation
  • Mechanistic study
  • Phosphoryl compounds

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