Electrochemical synthesis of new sulfone and sulfonamide derivatives. A green method based on the electrolysis of 2-amino-5-nitrophenol. (1st November 2021)

• Record Type: Journal Article
• Authors: Daneshyar, Anahita; Nematollahi, Davood; Bayat, Mahdi
• Is Part Of: Electrochimica acta. Volume 394(2021)
• Publication Date: 2021-11-01
• Subjects: Electrochemical synthesis -- 2-Amino-5-nitrophenol -- Diarylsulfone -- Michael addition reaction -- Sulfonamide -- Green chemistry; Electrochemistry -- Periodicals; Electrochemistry, Industrial -- Periodicals; 541.37
• DOI: 10.1016/j.electacta.2021.139223
• Languages: English
• ISSNs: 0013-4686

Abstract

Abstract: 2-Amino-5-nitrophenol (ANP) is an electrochemically interesting compound. It has a nitro group that can be reduced independently and also has hydroxyl and an amine functional groups, making the molecule susceptible to oxidation. These features allow us to easily synthesize new sulfonamide-diarylsulfone (SDS) and diarylsulfone (DAS) derivatives by a reduction/oxidation process or a single oxidation process, respectively. In the first process, the nitro group in the ANP is first reduced at the cathode and then oxidized at the anode. In these conditions, the generated Michael acceptor in the presence of arylsulfinic acids (ASAs) is converted to the corresponding SDS derivative. In the latter process, the ANP is directly oxidized at the anode, then the formed Michael acceptor in the presence of ASAs is converted to the corresponding DAS derivative. The electrochemical synthesis of SDS was successfully performed under environmentally friendly conditions, in one-pot, under constant current conditions, in an undivided cell at room temperature. The independent electrosynthesis of DAS was also successfully achieved in a divided cell under the conditions mentioned above, using an environmentally friendly approach. In this work we have introduced a flexible, highly efficient method for the synthesis of diarylsulfone derivatives. In addition, in this work, electrochemical behavior of ANP has been extensively studied. The results of these studies have led to the proposal of mechanisms for the electrochemical behavior of ANP in different conditions. Abstract : A green method based on the electrolysis of 2-amino-5-nitrophenol for synthesize of new sulfonamide-diarylsulfone and diarylsulfone derivatives. Image, graphical abstract .