3-Sulfonylindoles via Gold- or Silver-Catalyzed Cyclization─1,3-Sulfonyl Migration Sequences under Visible Light Irradiation
Fen Zhao, Wided Hagui, María Ballarín‐Marión, Cyril Ollivier, Virginie Mouriès‐Mansuy, Louis Fensterbank
Abstract
High Resolution Image Download MS PowerPoint Slide A pathway for the synthesis of 3-sulfonylindoles has been devised. Upon blue LED irradiation, in the presence of a gold(I) or a silver(I) salt, ortho -alkynyl N -sulfonyl precursors readily undergo a 5- endo - dig cyclization concomitant with a 1,3-sulfonyl migration. While the gold-catalyzed reaction takes place in photocatalyst-free conditions, an iridium photocatalyst (Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 ) is necessary with silver catalysis. Mechanistic studies featuring the generation of a sulfonyl radical support this dichotomy.
Topics & Concepts
SulfonylCatalysisPhotocatalysisChemistryIridiumPhotochemistryIrradiationCombinatorial chemistryMedicinal chemistryOrganic chemistryAlkylPhysicsNuclear physicsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions