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

Ke Gao, Takeshi Yamakawa, Naohiko Yoshikai

研究成果: Article査読

39 被引用数 (Scopus)

抄録

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.

本文言語English
論文番号ss-2014-z0228-fa
ページ(範囲)2024-2039
ページ数16
ジャーナルSynthesis (Germany)
46
15
DOI
出版ステータスPublished - 2014 8
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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