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Excited‐State 2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) Initiated Organic Synthetic Transformations under Visible‐Light Irradiation
Ist Teil von
European journal of organic chemistry, 2021-04, Vol.2021 (15), p.2145-2161
Ort / Verlag
Weinheim: Wiley Subscription Services, Inc
Erscheinungsjahr
2021
Link zum Volltext
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
The one‐electron oxidizing capacity of 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) improves significantly by visible‐light excitation. The exited‐state DDQ (DDQ*) even converts benzene, fluoroarenes, heteroarenes, benzyls, and olefins into their corresponding radical cations as well as chloride and other anions into their radicals. These reactive intermediates have been utilized for the generation of C−C and C−X (N, O, or Cl) bonds in the synthesis of valuable organic compounds and natural products. This mini review provides an overview of such DDQ*‐initiated organic transformations with their scope and limitations and discusses the proposed reactions mechanisms.
2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) is a classic oxidation reagent in organic synthesis. Upon visible light excitation its oxidation potential is boosted beyond+3 V vs SCE. This property has been used for oxidative organic transformations and catalyst regeneration is achieved by air oxygen or electrochemically.