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Electroreduction Enables Regioselective 1,2-Diarylation of Alkenes with Two Electrophiles.

Weijie YuShengchun WangMeng HeZhou JiangYi YuJinping LanJin LuoPengjie WangXiaotian QiTao WangAiwen Lei
Published in: Angewandte Chemie (International ed. in English) (2023)
Precisely introducing two similar functional groups into bulk chemical alkenes represents a formidable route to complex molecules. Especially, the selective activation of two electrophiles is in crucial demand, yet challenging for cross-electrophile-coupling. Herein, we demonstrate a redox-mediated electrolysis, in which aryl nitriles are both aryl radical precursors and redox-mediators, enables an intermolecular alkene 1,2-diarylation with a remarkable regioselectivity, thereby avoiding the involvement of transition-metal catalysts. This transformation utilizes cyanoarene radical anions for activating various aryl halides (including iodides, bromides, and even chlorides) and affords 1,2-diarylation adducts in up to 83 % yield and >20 : 1 regioselectivity with more than 80 examples, providing a feasible approach to complex bibenzyl derivatives.
Keyphrases
  • transition metal
  • signaling pathway
  • ionic liquid
  • metal organic framework
  • energy transfer