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Literature DB >> 24625055

Direct C-N coupling of imidazoles with aromatic and benzylic compounds via Electrooxidative C-H functionalization.

Tatsuya Morofuji¹, Akihiro Shimizu, Jun-ichi Yoshida.

Abstract

A method for the C-N coupling of imidazoles based on electrooxidative C-H functionalization of aromatic and benzylic compounds has been developed. The key to the success is the formation of protected imidazolium ions as initial products, avoiding overoxidation. Deprotection under nonoxidative conditions affords N-substituted imidazoles. Various functional groups are compatible with the present transformation. To demonstrate the power of the method, a P450 17 inhibiter and an antifungal agent having N-substituted imidazole structures were synthesized.

Entities: Chemical

Mesh：

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Year: 2014 PMID： 24625055 DOI： 10.1021/ja501093m

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

21 in total

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5. Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis.

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Journal: J Am Chem Soc Date: 2017-02-14 Impact factor: 15.419

Review 6. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors: Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal: Chem Rev Date: 2021-08-10 Impact factor: 60.622

Direct C-N coupling of imidazoles with aromatic and benzylic compounds via Electrooxidative C-H functionalization.

Review 1. Expanding the medicinal chemistry synthetic toolbox.

2. Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

3. Electrochemically Enabled, Nickel-Catalyzed Amination.

Review 4. Synthetic Organic Electrochemistry: Calling All Engineers.

5. Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis.

Review 6. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

7. Site-Selective Synthesis of N-Benzyl 2,4,6-Collidinium Salts by Electrooxidative C-H Functionalization.

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

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

10. Radical C-H functionalization of heteroarenes under electrochemical control.