Palladium(II)-catalyzed direct ortho-C-H acylation of anilides by oxidative cross-coupling with aldehydes using tert-butyl hydroperoxide as oxidant

Chun Wo Chan, Zhongyuan Zhou, Wing Yiu Yu

Research output: Journal article publicationJournal articleAcademic researchpeer-review

120 Citations (Scopus)

Abstract

An efficient palladium-catalyzed C-H acylation with aldehydes using tert-butyl hydroperoxide (TBHP) transforms various anilides into synthetically useful 2-aminobenzophenone derivatives under mild conditions (40°C, 3 h). The acylation reaction exhibits excellent regioselectivity and functional group tolerance, and simple aromatic aldehydes, functionalized aliphatic aldehydes and heteroaromatic aldehydes are effective coupling partners. The acylation reaction is probably initiated by a rate-limiting electrophilic C-H cyclopalladation (kH/kD=3.6; ρ+=-0.74) to form an arylpalladium complex, followed by acyl radical functionalization.
Original languageEnglish
Pages (from-to)2999-3006
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number16
DOIs
Publication statusPublished - 1 Nov 2011

Keywords

  • 2-aminobenzophenones
  • acylation
  • C-H activation
  • Friedel-Crafts reaction
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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