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Nucleophilic Radicals as Hydrogen Atom Abstractors in C(sp<sup>3</sup>)‐H Functionalization Reactions

Tao Li, Jian Li, Haohua Huo

2022Chinese Journal of Chemistry14 citationsDOI

Abstract

Comprehensive Summary Hydrogen atom transfer (HAT) is an elementary mechanistic step in organic synthesis. The photoredox‐catalyzed HAT has transformed organic synthesis by enabling the activation and subsequent cross‐coupling of traditionally inert yet ubiquitous C(sp 3 )‐H bonds. While diverse electrophilic radical species have proven to be exceptionally effective HAT catalysts for selective functionalization of hydridic and electron‐neutral C(sp 3 )‐H, general methods using nucleophilic radicals as hydrogen atom abstractors in C(sp 3 )‐H functionalization remain relatively underdeveloped. Herein, we highlight two creative and strategic advances in addressing this long‐standing challenge, and emphasize reaction achievements, mechanistic insights, potential, and future challenges.

Topics & Concepts

ChemistryElectrophileSurface modificationNucleophileHydrogen atomRadicalCatalysisOrganic synthesisPhotoredox catalysisPhotochemistryCombinatorial chemistryOrganic chemistryPhysical chemistryGroup (periodic table)PhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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