Learning From Vitamin B 12 -Mediated Reactions: Cobalt(III)−Carbon-Assisted Catalytic C−H Difluoroacylation of (Hetero)Arenes through Controlled-Potential Electrolysis

Md Jakir Hossain, Toshikazu Ono, Yoshio Yano, Yoshio Hisaeda

研究成果: Contribution to journalArticle

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The synthesis of difluoromethylated (CF 2 R) (R=H, alkyl/aryl, CO 2 R, etc.) compounds has received considerable attention in recent years. In this study, the cobalt(III)−carbon-mediated catalytic C−H difluoroacylation of unactivated arenes and heteroarenes using BrCF 2 CO 2 Et is reported. This catalytic cycle is based on a valence change of the cobalt catalyst, a naturally derived vitamin B 12 derivative, driven by controlled-potential electrolysis at −0.8 V vs. Ag/AgCl under visible-light irradiation in dimethyl sulfoxide. A broad substrate scope is demonstrated, and two compounds were characterized according to their X-ray crystal structures. Mechanistic studies showed that the reaction proceeds through a radical pathway mediated by homolytic cleavage of the cobalt(III)–carbon bond. A turnover number of more than 100 was observed, owing to the inherent stability of the vitamin B 12 framework. This naturally derived catalytic system has potential applications in medicinal chemistry and materials science.

元の言語英語
ジャーナルChemElectroChem
DOI
出版物ステータス出版済み - 1 1 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electrochemistry

フィンガープリント Learning From Vitamin B <sub>12</sub> -Mediated Reactions: Cobalt(III)−Carbon-Assisted Catalytic C−H Difluoroacylation of (Hetero)Arenes through Controlled-Potential Electrolysis' の研究トピックを掘り下げます。これらはともに一意のフィンガープリントを構成します。

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