Excited-State 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ*) Initiated Organic Synthetic Transformations under Visible-Light Irradiation

Natarajan, Palani and Koenig, 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. ISSN 1434-193X, 1099-0690

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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 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.

Item Type: Article
Uncontrolled 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
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Petra Gürster
Date Deposited: 10 Jan 2023 11:16
Last Modified: 10 Jan 2023 11:16
URI: https://pred.uni-regensburg.de/id/eprint/46767

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