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

European Journal of Organic Chemistry · 2017 · Vol. 2017(15) · pp. 2056–2071
Luca CapaldoDavide Ravelli

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 <i>direct</i> strategy, based on the intrinsic reactivity of a limited number of photocatalysts in the excited state, or an <i>indirect</i> 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.

Radical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsChemistryPhotocatalysisOrganic synthesisHalogenCatalysisSubstrate (aquarium)Hydrogen atomReactivity (psychology)Excited stateFluorine

Funding

  • Ministero dell’Istruzione, dell’Università e della Ricerca
  • Università degli Studi di Pavia
  • Ministero dell'Università e della Ricerca
Citations
766
FWCI
22.97
field-weighted impact
References
101
Percentile
100%
vs. same field & year
Citations per year
References
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