Palladium-Catalyzed Site-Selective [5 + 1] Annulation of Aromatic Amides with Alkenes: Acceleration of β-Hydride Elimination by Maleic Anhydride from Palladacycle

Qiyuan He, Ken Yamazaki, Yusuke Ano, Naoto Chatani

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The palladium-catalyzed reaction of 2-methylbenzamides with acrylic esters, leading to the production of isoquinolinones, is reported. The reaction occurs exclusively at the ortho methyl C–H bond via a six-membered palladacycle and not at the ortho C–H bond via a five-membered palladacycle. A key to the success of the reaction is the use of maleic anhydride as a ligand. Computational analyses suggest that the coordination of the maleic anhydride ligand highly stabilizes the transition state for β-hydride elimination and accelerates the β-hydride elimination.

Original languageEnglish
Pages (from-to)1595-1600
Number of pages6
JournalACS Catalysis
Volume12
Issue number2
DOIs
Publication statusPublished - Jan 21 2022
Externally publishedYes

Keywords

  • annulation
  • C−H activation
  • maleic anhydride
  • palladium
  • β-hydride elimination

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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