197727-60-9Relevant 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 %.
Indole Resin: A Versatile New Support for the Solid-Phase Synthesis of Organic Molecules
Estep, Kimberly G.,Neipp, Christopher E.,Stephens Stramiello, Linda M.,Adam, Mavis D.,Allen, Martin P.,Robinson, Shaughnessy,Roskamp, Eric J.
, p. 5300 - 5301 (2007/10/03)
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