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A General Platform for Visible Light Sulfonylation Reactions Enabled by Catalytic Triarylamine EDA Complexes

Juan D. Lasso, Durbis J. Castillo‐Pazos, Jan Michael Salgado, Cory Ruchlin, Loric Lefebvre, Daliah Farajat, Dmitrii F. Perepichka, Chao‐Jun Li

2024Journal of the American Chemical Society119 citationsDOI

Abstract

Catalytic electron donor-acceptor (EDA) complexes have recently emerged as a powerful and sustainable alternative to iridium- and ruthenium-based photoredox synthetic methods. Yet, these complexes remain underexplored and reliant on the use of meticulously designed acceptors that require previous installation. Herein, we report a novel EDA complex employing tris(4-methoxyphenyl) amine as a catalytic donor for the sulfonylation of alkenes using inexpensive and readily available sulfonyl chlorides. Applying this operationally simple, visible-light-mediated general platform, we report both the redox-neutral and net-reductive functionalization of more than 60 substrates, encompassing vinylic or allylic sulfonylation, hydrosulfonylation, and sulfamoylation of activated and unactivated alkenes and alkynes.

Topics & Concepts

ChemistryAllylic rearrangementRutheniumCatalysisSulfonylAmine gas treatingCombinatorial chemistryIridiumAcceptorPhotochemistryPhotoredox catalysisOrganic chemistryPhotocatalysisPhysicsCondensed matter physicsAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
A General Platform for Visible Light Sulfonylation Reactions Enabled by Catalytic Triarylamine EDA Complexes | Litcius