Aerobic, transition-metal-free, direct, and regiospecific mono-α-arylation of ketones: Synthesis and mechanism by DFT calculations

Qing Long Xu, Hongyin Gao, Muhammed Yousufuddin, Daniel H. Ess, László Kürti

Research output: Contribution to journalArticle

64 Scopus citations

Abstract

We disclose a facile, aerobic, transition-metal-free, direct, and regiospecific mono-α-arylation of ketones to yield aryl benzyl and (cyclo)alkyl benzyl ketones with substitution patterns that are currently inaccessible or challenging to prepare using conventional methods. The transformation is operationally simple, scalable, and environmentally friendly. There is no need for pre-functionalization (i.e., α-halogenation or silyl enol ether formation) or the use of specialized arylating agents (i.e., diaryliodonium salts). DFT calculations suggest that the in situ-generated enolate undergoes direct C-C bond formation with the nitroarene followed by regioselective O2-mediated C-H oxidation.

Original languageEnglish (US)
Pages (from-to)14048-14051
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number38
DOIs
StatePublished - Sep 25 2013

ASJC Scopus subject areas

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

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