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Literature DB >> 30650241

Photoelectrochemical C-H Alkylation of Heteroarenes with Organotrifluoroborates.

Hong Yan¹, Zhong-Wei Hou¹, Hai-Chao Xu¹.

Abstract

A photoelectrochemical method for the C-H alkylation of heteroarenes with organotrifluoroborates has been developed. The merger of electrocatalysis and photoredox catalysis provides a chemical oxidant-free approach for the generation and functionalization of alkyl radicals from organotrifluoroborates. A variety of heteroarenes were functionalized using primary, secondary, and tertiary alkyltrifluoroborates with excellent regio- and chemoselectivity.

Entities: Chemical

Keywords: C−H alkylation; electrochemistry; oxidation; photoelectrochemistry; radical reactions

Year: 2019 PMID： 30650241 DOI： 10.1002/anie.201814488

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

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Cited

26 in total

1. Electrophotocatalytic diamination of vicinal C-H bonds.

Authors: Tao Shen; Tristan H Lambert
Journal: Science Date: 2021-02-04 Impact factor: 47.728

2. Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols.

Authors: Wen Zhang; Keith L Carpenter; Song Lin
Journal: Angew Chem Int Ed Engl Date: 2019-11-18 Impact factor: 15.336

3. Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

Authors: Jonathan J Kennedy-Ellis; Erik D Boldt; Sherry R Chemler
Journal: Org Lett Date: 2020-10-19 Impact factor: 6.005

Review 4. 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

Photoelectrochemical C-H Alkylation of Heteroarenes with Organotrifluoroborates.

1. Electrophotocatalytic diamination of vicinal C-H bonds.

2. Electrochemistry Broadens the Scope of Flavin Photocatalysis: Photoelectrocatalytic Oxidation of Unactivated Alcohols.

3. Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

Review 4. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

5. Electrophotocatalytic S_N Ar Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base.

6. Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling.

7. Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity.

8. Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins.

9. Electrophotocatalytic C-H Heterofunctionalization of Arenes.

Review 10. Oxidase reactions in photoredox catalysis.