Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation

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.

Regulation of Photogenerated Redox Species through High Crystallinity Carbon Nitride for Improved C−S Coupling Reactions

“…The authors have cited additional references within the Supporting Information (Ref. [30][31][32][33][34][35][36][37][38][39][40][41][42][43]).…”

Visible‐Light‐Mediated Synthesis of Bicalutamide by Regioselective Hydroxysulfonylation of Acrylamides

“…Additional references cited within the Supporting Information. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44]…”

Solvent-controlled regioselective C(5)–H/N(1)–H bond alkylations of indolines and C(6)–H bond alkylations of 1,2,3,4-tetrahydroquinolines with para-quinone methides

“…8 Since the C5-position of indole is far away from the C3-site, installing a DG to access C(5)–H functionalization is limited. So far, alkylation, 9 allylation, 10 olefination, 11 sulfonylation, 12 selenation, 13 and sulfonylmethylation 14 at the C5-position of indole have been performed. Similarly, the functionalization of THQ at the C6-position has also been rarely studied.…”