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Title
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Electrochemical synthesis of 1-N-phenyl-4- (sulfonyl)benzene-1,2-diamine derivatives: a mild and regioselective protocol
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Type
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JournalPaper
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Keywords
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Electrosynthesis; 2-Aminodiphenylamine; Regioselective synthesis; pair convergent reaction
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Abstract
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Regioselective synthesis of 1-N-phenyl-4-(sulfonyl)benzene-1,2-diamine derivatives was carried out by the anodic oxidation of 2-aminodiphenylamine in a water/ethanol mixture in the presence of sulfinic acids as nucleophiles using both controlled-potential and constant current techniques. Our voltammetric data indicate that the anodic oxidation of 2-aminodiphenylamine produces 1-N-phenyl-o-benzoquinone diamine. This compound acts as a Michael acceptor providing 1-N-phenyl-4-(arylsulfonyl)benzene-1,2- diamines in high yields. In this new methodology, a mixture of water and ethanol was used as the solvent, a carbon rod was used as the anode and the use of toxic and/or hazardous reagents was avoided.
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Researchers
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Elam Salahifar (Fourth Researcher), Davood Nematollahi (Second Researcher), Farzad Nikpour (Third Researcher), Mahnaz Sharafi (First Researcher)
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