Electrochemical Cross‐Coupling of C(sp2)−H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox‐Based Approach

Abstract Photoredox‐based C−H bond functionalization constitutes one of the most powerful and atom‐economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst ( PC ) and redox‐ active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross‐coupling of C( sp 2 )−H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci‐type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale‐up. These results demonstrate that photoredox‐based cross‐coupling of C( sp 2 )−H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. magnified image