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Synthetic Applications of Photochemically Generated Radicals from Protic C(sp<sup>3</sup>)−H Bonds

Tegan E. O’Brien, Avery O. Morris, Lucas F. Villela, Louis Barriault

2023ChemCatChem30 citationsDOI

Abstract

Abstract The utilization of photo‐induced processes in C−H functionalization via radical pathways has emerged as a highly promising strategy for the preparation and modification of complex organic compounds. While current methods for generating carbon‐centred radicals from C−H bonds primarily focus on hydridic C−H bonds to yield nucleophilic radical species, the reactivity and potential applications of electrophilic radicals derived from protic C−H bonds remain largely unexplored. In this review, we aim to shed light on the seminal findings regarding the activation of protic C(sp 3 )−H bonds while also showcasing noteworthy examples of this radical formation process. Mechanistically diverse modes of activation are discussed, unified by proton‐coupled electron transfer (PCET) concepts.

Topics & Concepts

RadicalChemistryElectrophileNucleophilePhotochemistryReactivity (psychology)Surface modificationProtonYield (engineering)Electron transferProton-coupled electron transferOrganic synthesisOrganic chemistryCatalysisPhysical chemistryMetallurgyAlternative medicinePathologyMaterials scienceMedicinePhysicsQuantum mechanicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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