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Novel Synthesis of Mafenide and Other Amino Sulfonamides by Electrochemical Reduction of Cyano Sulfonamides
Author(s) -
Lateef Shaik,
Mohan Srinivasulu Reddy Krishna,
Rameshraju Rudraraju,
Reddy Srinivasulu Reddy Jayarama
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690123
Subject(s) - chemistry , nitrile , electrochemistry , catalysis , anode , cathode , selectivity , catalytic hydrogenation , environmentally friendly , organic chemistry , combinatorial chemistry , electrode , ecology , biology
Both aliphatic and aromatic amino sulfonamides such as mafenide ( 1a ) were synthesized in good yields (80–86%) by direct electrochemical hydrogenation of the corresponding nitriles in an undivided cell containing a Ni cathode, a Pt anode, and Raney Ni as catalyst ( Table 1 ). The reaction can be performed without external supply of pressurized gas by in situ generation of H 2 . Slightly elevated temperatures (45°) and low current densities (10 mA/cm 2 ) are favorable conditions for this type of electrochemical nitrile hydrogenation. Our synthetic protocol does not require high‐pressure equipment or chemical hazards, is environmentally very friendly, and more economical than traditional methods. The concentration of adsorbed H . radicals on the catalyst surface can be easily controlled by adjusting the electric potential, which may lead to improved product selectivity and, at the same time, reduces the risk of explosion and fire.