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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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| Item type | Article | ||||
| Journal or Publication Title | European Journal of Organic Chemistry | ||||
| Publisher: | Wiley | ||||
|---|---|---|---|---|---|
| Place of Publication: | WEINHEIM | ||||
| Volume: | 2021 | ||||
| Number of Issue or Book Chapter: | 15 | ||||
| Page Range: | pp. 2145-2161 | ||||
| Date | 22 April 2021 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identification Number |
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| Keywords | ELECTRON-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 Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Partially | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-449076 | ||||
| Item ID | 44907 |
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