Litcius/Paper detail

Sulfonium Salts as Acceptors in Electron Donor‐Acceptor Complexes

Leendert van Dalsen, Rachel E. Brown, James A. Rossi‐Ashton, David J. Procter

2023Angewandte Chemie International Edition192 citationsDOIOpen Access PDF

Abstract

The photoactivation of electron donor-acceptor complexes has emerged as a sustainable, selective and versatile strategy for the generation of radical species. Electron donor-acceptor (EDA) complexation, however, imposes electronic constraints on the donor and acceptor components and this can limit the range of radicals that can be generated using the approach. New EDA complexation strategies exploiting sulfonium salts allow radicals to be generated from native functionality. For example, aryl sulfonium salts, formed by the activation of arenes, can serve as the acceptor components in EDA complexes due to their electron-deficient nature. This "sulfonium tag" approach relaxes the electronic constraints on the parent substrate and dramatically expands the range of radicals that can be generated using EDA complexation. In this review, these new applications of sulfonium salts will be introduced and the areas of chemical space rendered accessible through this innovation will be highlighted.

Topics & Concepts

SulfoniumAcceptorChemistryElectron acceptorRadicalArylElectron donorPhotochemistryCombinatorial chemistrySubstrate (aquarium)Organic chemistryCatalysisSalt (chemistry)AlkylOceanographyGeologyPhysicsCondensed matter physicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods