C–C and C–N bond formation in electro-oxidation reactions of aromatic compounds

Q2 Materials Science

Current Research in Green and Sustainable Chemistry Pub Date : 2024-01-01 DOI:10.1016/j.crgsc.2024.100406

A. Kononov , S. Strekalova , E. Kobeleva , G. Savelyev , A. Zlygostev , M. Khvorova , V. Morozov , O. Babaeva , Y. Budnikova

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Abstract

Atom-economical, eco-efficient, metal- and chemical oxidant-free formation of C–C and C–N bond from C(sp²)−H and C(sp³)−H of arenes toward the direct synthesis of biaryls and anilides or N-benzylamides under mild electro-oxidative conditions is described. The products of C–C and C–N coupling are obtained in up to 88% yields. Aromatic substrates that are oxidized at potentials less positive than +2 V or have bulky bromine or iodine substituents undergo homo-coupling reactions by anodic oxidation to form biaryls or dimers. Aromatic substrates that are difficult to oxidize (E_ox > +2 V) preferentially form anilides and N-benzylamides upon anodic oxidation. The presence of a chlorine substituent on the aromatic ring leads to the formation of both biaryls and anilides during electro-oxidation.

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芳香族化合物电氧化反应中 C-C 和 C-N 键的形成

该研究描述了在温和的电氧化条件下，以原子经济、生态高效、不含金属和化学氧化剂的方式，从茴香的 C(sp)-H 和 C(sp)-H 生成 C-C 和 C-N 键，从而直接合成双芳基化合物和苯胺或苄酰胺。C-C 和 C-N 偶联产物的收率高达 88%。在电位小于 +2 V 的条件下氧化的芳香族底物或具有笨重溴或碘取代基的芳香族底物会通过阳极氧化发生同偶联反应，形成双芳基或二聚体。难以氧化（> +2 V）的芳香底物在阳极氧化时会优先形成苯胺和苄酰胺。芳香环上氯取代基的存在会导致在电氧化过程中形成双芳基和苯胺。

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