A vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media,Chemical Communications

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A vitamin B12 derivative catalyzed electrochemical trifluoromethylation and perfluoroalkylation of arenes and heteroarenes in organic media
Chemical Communications ( IF 4.3 ) Pub Date : 2017-09-13 00:00:00 , DOI: 10.1039/c7cc06221d
Md. Jakir Hossain _{1,

2,

3,

4,

5} , Toshikazu Ono _{1,

2,

3,

4,

5} , Kosuke Wakiya _{1,

2,

3,

4,

5} , Yoshio Hisaeda _{1,

2,

3,

4,

5}

Affiliation

The electrochemical trifluoromethylation and perfluoroalkylation of aromatic compounds mediated by a vitamin B₁₂ derivative as a cobalt-based catalyst has been developed. The Co(I) species of a vitamin B₁₂ derivative, prepared by controlled-potential electrolysis at −0.8 V vs. Ag/AgCl in methanol, reacted with R_fI (R_f = CF₃, n-C₃F₇, n-C₄F₉, n-C₈F₁₇, and n-C₁₀F₂₁) to form a Co–R_f complex. This complex released an R_f radical under visible light irradiation, which then reacted directly with non-activated (hetero)arenes to form the desired fluoroalkylated molecules through direct C–H functionalization. To our knowledge, this is the first report of a naturally derived vitamin B₁₂ catalyzed trifluoromethylation and perfluoroalkylation of aromatic compounds as a cobalt-mediated catalyst.

中文翻译：

维生素B ₁₂衍生物在有机介质中催化芳烃和杂芳烃的电化学三氟甲基化和全氟烷基化

已经开发了由维生素B ₁₂衍生物作为钴基催化剂介导的芳香族化合物的电化学三氟甲基化和全氟烷基化。维生素B ₁₂衍生物的Co（I）物种是通过在甲醇中于-0.8 V相对于Ag / AgCl的受控电势电解制备的，与R _f I（R _f = CF ₃，n -C ₃ F ₇，n -C ₄ F ₉，n -C ₈ F ₁₇和n -C ₁₀ F ₂₁）形成Co-R _f络合物。该复合物在可见光照射下释放出一个R _f基团，然后通过未反应的（杂）芳烃直接与CH官能团直接反应，形成所需的氟代烷基化分子。据我们所知，这是天然来源的维生素B ₁₂催化三价甲基化和芳族化合物作为钴介导的催化剂的全氟烷基化的首次报道。

更新日期：2017-09-20

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