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

Ke Gao, Takeshi Yamakawa, Naohiko Yoshikai

研究成果: ジャーナルへの寄稿学術論文査読

44 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.

本文言語英語
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
46
15
DOI
出版ステータス出版済み - 2014 8月

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