Electrochemical borylation of nitroarenes

Transition Metal‐Free Aromatic C−H, C−N, C−S and C−O Borylation

“…Very recently, our group achieved the metal-free CÀ N borylation of nitroarenes employing electrochemical conditions (Scheme 24). [49] The electrochemical borylation of a diverse range of nitroarenes including bioactive molecules are furnished at room temperature under simple conditions, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies indicated that nitroarenes were reduced into anilines by electron and B 2 pin 2 at the cathode, which further underwent radical borylation to afford aryl boron products with the aid of tert-butyl nitrite ( t BuONO) and B 2 pin 2 .…”

Electrochemical synthesis and transformation of organoboron compounds

“…Very recently, the same group achieved the electrochemical borylation of nitroarenes to prepare aryl boronic esters in moderate to good yields with good functional group tolerance (Scheme 7b). 21 The late-stage borylation and derivatization of bioactive molecules demonstrated the broad utility of this protocol. The direct utilization of the “synthetically upstream” nitroarenes in borylation transformation would substantially impact the conventional processes for synthesizing functionalized arenes.…”

Progress in the Electrochemical Synthesis of Organoboron Compounds

“…Arylhydrazine with substituents such as methyl, butyl, halides, methoxy, -CF 3 , and -OCF 3 was susceptible with moderate yields of the targeted products Mechanistic detail was investigated with several techniques, such as cyclic voltammetry, radical trapping experiments. As such, the electrochemical CÀ N borylation started with the anodic oxidation of phenylhydrazine 61 to create the phenyl radical 62 with the A simple and efficient electrochemical method for converting nitroarenes into aryl boronic esters, with good functional group tolerance and applicability to a wide range of substrates (Scheme 18) [79] was developed. This electrochemical borylation method was used to successfully convert nitrobenzene with methyl groups in different positions to the corresponding borylated products.…”

“…A simple and efficient electrochemical method for converting nitroarenes into aryl boronic esters, with good functional group tolerance and applicability to a wide range of substrates (Scheme 18) [79] was developed. This electrochemical borylation method was used to successfully convert nitrobenzene with methyl groups in different positions to the corresponding borylated products.…”