540514-29-2Relevant articles and documents
Metal-Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO2, and Amines
Blum, Stephan P.,Karakaya, Tarik,Schollmeyer, Dieter,Klapars, Artis,Waldvogel, Siegfried R.
supporting information, p. 5056 - 5062 (2021/02/05)
Sulfonamides are among the most important chemical motifs in pharmaceuticals and agrochemicals. However, there is no methodology to directly introduce the sulfonamide group to a non-prefunctionalized aromatic compound. Herein, we present the first dehydrogenative electrochemical sulfonamide synthesis protocol by exploiting the inherent reactivity of (hetero)arenes in a highly convergent reaction with SO2 and amines via amidosulfinate intermediate. The amidosulfinate serves a dual role as reactant and supporting electrolyte. Direct anodic oxidation of the aromatic compound triggers the reaction, followed by nucleophilic attack of the amidosulfinate. Boron-doped diamond (BDD) electrodes and a HFIP–MeCN solvent mixture enable selective formation of the sulfonamides. In total, 36 examples are demonstrated with yields up to 85 %.
Palladium-catalysed dehydrogenative sp3 C-H bonds functionalisation into alkenes: A direct access to N-alkenylbenzenesulfonamides
Bheeter, Charles B.,Jin, Rongwei,Bera, Jitendra K.,Dixneuf, Pierre H.,Doucet, Henri
, p. 119 - 124 (2014/03/21)
The palladium-catalysed dehydrogenation of sp3 carbon-hydrogen bonds of N-alkylbenzenesulfonamides allows a simple access to N-alkenylbenzenesulfonamides. The reaction proceeds with easily accessible catalysts, with pivalate as a base, and allo
