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Natarajan, Palani ; König, Burkhard

Excited‐state 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ*) initiated organic synthetic transformations under visible‐light irradiation

Natarajan, Palani and König, Burkhard (2021) Excited‐state 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ*) initiated organic synthetic transformations under visible‐light irradiation. European Journal of Organic Chemistry 2021 (15), pp. 2145-2161.

Date of publication of this fulltext: 19 Feb 2021 05:50
Article
DOI to cite this document: 10.5283/epub.44907


Abstract

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 ...

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.



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Details

Item typeArticle
Journal or Publication TitleEuropean Journal of Organic Chemistry
Publisher:Wiley
Place of Publication:WEINHEIM
Volume:2021
Number of Issue or Book Chapter:15
Page Range:pp. 2145-2161
Date22 April 2021
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Identification Number
ValueType
10.1002/ejoc.202100011DOI
KeywordsELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; P-BENZOQUINONE; BENZENE; HYDROXYLATION; OXIDATION; ARENES; 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE; REACTIVITY; COMPLEXES; Cross coupling; DDQ; Dehydrogenative coupling; Photooxidation; Quinones
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgPartially
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-449076
Item ID44907

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