Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides
Alyssa F. J. van den Boom, Han Zuilhof
Abstract
High Resolution Image Download MS PowerPoint Slide Sulfonamides have many important biological applications, yet their synthesis often involves long reaction times under dry and non-ambient conditions. Here we report the synthesis of a large range of sulfonamides at room temperature using 4-nitrophenyl benzylsulfonate as a starting material. Sulfonamides were prepared from a wide range of aliphatic, linear, and cyclic amines, anilines, and N -methylanilines. The yields and reaction times observed here were comparable to or better than those reported previously, establishing sulfur-phenolate exchange as a viable alternative.
Topics & Concepts
ChemistrySulfurSulfonamideCombinatorial chemistryReaction conditionsOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesChemical Synthesis and AnalysisCatalytic Cross-Coupling Reactions