Electrochemical synthesis of new sulfone and sulfonamide derivatives. A green method based on the electrolysis of 2-amino-5-nitrophenol

Electrochemical Synthesis of Sulfonamide Derivatives: Electrosynthesis Conditions and Reaction Pathways

“…This molecule has two oxidizable (À NH 2 and À OH) and one reducible (À NO 2 ) groups in appropriate positions relative to each other which makes the electrochemistry of this compound interesting. [69] The presence of these groups makes new derivatives of sulfonamide-sulfone and diaryl sulfone to be synthesized by a paired electrochemical process or a single oxidation process, respectively. When this molecule is electrolyzed in an undivided cell in the presence of arylsulfnic acids, it is converted to a sulfonamide-sulfone (SUL) compound according to the following mechanism (Scheme 30).…”

“…One of the most interesting case in terms of synthesis as well as mechanism is the electrochemical study of 2‐amino‐5‐nitrophenol ( ANP ) in the presence of arylsulfinic acids ( ASA ). This molecule has two oxidizable (−NH 2 and −OH) and one reducible (−NO 2 ) groups in appropriate positions relative to each other which makes the electrochemistry of this compound interesting [69] . The presence of these groups makes new derivatives of sulfonamide‐sulfone and diaryl sulfone to be synthesized by a paired electrochemical process or a single oxidation process, respectively.…”

“… Proposed mechanism for the direct oxidation of ANP in the divided cell in the presence of arylsulfinic acids [69] …”

A Green Electrochemical Method for the Synthesis of New Sulfonamide and Disulfonamide Derivatives Based on the Oxidation of Phenylhydrazine Derivatives and Evaluation of their Antibacterial Activity

“…To solve these problems, we and others have tried to synthesize new sulfonamide derivatives by electrochemical methods in accordance with the principles of green chemistry. [13][14][15][16][17][18][19][20][21][22][23][24][25][26] In these papers, the electrochemical synthesis of a large number of sulfonamides, some of which have been tested and proven to have antibacterial properties, have been reported using different reagents and in different procedures. Electrosynthesis provides a green, mild and efficient protocol for the synthesis of simple and complex organic molecules, and thus suppresses the use of harsh chemical oxidants and reductants in traditional synthetic methods.…”