Cobalt-catalyzed chelation-assisted alkylation of arenes with primary and secondary alkyl halides

Ke Gao, Takeshi Yamakawa, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Cobalt-N-heterocyclic carbene catalytic systems have been developed for chelation-assisted ortho-alkylation of aromatic compounds with alkyl halides. Aryl imines can be selectively monoalkylated at room temperature by various primary or secondary alkyl chlorides or bromides. The catalytic system can also be applied to 2-arylpyridine derivatives, which in the absence of steric hindrance are amenable to dialkylation by an excess of the alkyl halide. Mechanistic experiments, including reactions of stereochemical probes and radical clocks, indicate that the reaction involves single-electron transfer from the cobalt center to the alkyl halide to form the corresponding alkyl radical, which has a finite lifetime before it undergoes C-C bond formation.

Original languageEnglish
Article numberss-2014-z0228-fa
Pages (from-to)2024-2039
Number of pages16
JournalSynthesis (Germany)
Volume46
Issue number15
DOIs
Publication statusPublished - 2014 Aug
Externally publishedYes

Keywords

  • alkyl halides
  • alkylations
  • catalysis
  • cobalt
  • functionalization
  • radical reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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