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Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

Luca Capaldo, Davide Ravelli

2017European Journal of Organic Chemistry793 citationsDOIOpen Access PDF

Abstract

The adoption of hydrogen atom transfer (HAT) in a photocatalytic approach, in which an excited catalyst is responsible for substrate activation, offers unique opportunities in organic synthesis, enabling the straightforward activation of R–H (R = C, Si, S) bonds in desired reagents. Either a direct strategy, based on the intrinsic reactivity of a limited number of photocatalysts in the excited state, or an indirect one, in which a photocatalytic cycle is used for the generation of a thermal hydrogen abstractor, can be exploited. This microreview summarizes the most recent advances (mainly from the last two years) in this rapidly developing area of research, collecting the selected examples according to the nature of the species promoting the HAT process. From the synthetic point of view, this area has led to the development of a plethora of strategies for C–C, C–Si, C–N, C–S, and C–halogen (particularly, fluorine) bond formation, as well as for oxidation reactions.

Topics & Concepts

ChemistryPhotocatalysisOrganic synthesisHalogenCatalysisSubstrate (aquarium)Hydrogen atomReactivity (psychology)Excited stateFluorineReagentPhotochemistryCatalytic cycleCombinatorial chemistryNanotechnologyOrganic chemistryMaterials scienceAtomic physicsAlkylPathologyOceanographyAlternative medicinePhysicsMedicineGeologyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods