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Literature DB >> 26474405

Visible-Light-Catalyzed Direct Benzylic C(sp(3))-H Amination Reaction by Cross-Dehydrogenative Coupling.

Abstract

A conceptually new and synthetically valuable cross-dehydrogenative benzylic C(sp(3))-H amination reaction is reported by visible-light photoredox catalysis. This protocol employs DCA (9,10-dicyanoanthracene) as a visible-light-absorbing photoredox catalyst and an amide as the nitrogen source without the need of either a transition metal or an external oxidant.

Entities: Chemical Species

Keywords: C-H functinalization; amination; cross-coupling; photoredox catalysis; synthetic methods

Year: 2015 PMID： 26474405 DOI： 10.1002/anie.201506990

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

17 in total

Review 1. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors: Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal: Chem Rev Date: 2021-11-23 Impact factor: 60.622

Review 2. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors: Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal: Chem Rev Date: 2021-10-08 Impact factor: 60.622

Visible-Light-Catalyzed Direct Benzylic C(sp(3))-H Amination Reaction by Cross-Dehydrogenative Coupling.

Review 1. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Review 2. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

3. Red Light-Based Dual Photoredox Strategy Resembling the Z-Scheme of Natural Photosynthesis.

4. Ritter-type amination of C(sp³)-H bonds enabled by electrochemistry with SO₄².

5. Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation.

6. Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

7. Triiodide-Mediated δ-Amination of Secondary C-H Bonds.

Review 8. Photoredox-Catalyzed C-H Functionalization Reactions.

9. A unified photoredox-catalysis strategy for C(sp³)-H hydroxylation and amidation using hypervalent iodine.

10. Selective Photooxidation Reactions using Water-Soluble Anthraquinone Photocatalysts.