Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation
Paul Bourbon, Emeline Appert, Agnès Martin‐Mingot, Bastien Michelet, Sébastien Thibaudeau
Abstract
Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.
Topics & Concepts
SuperacidChemistryProtonationRegioselectivityAnilineElectrophilic aromatic substitutionIndole testElectrophileSurface modificationCombinatorial chemistryElectrophilic substitutionOrganic chemistryCatalysisPhysical chemistryIonSulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods