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Literature DB >> 33661562

Electrophotocatalytic C-H Heterofunctionalization of Arenes.

Abstract

The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, arenes undergo oxidant-free hydroxylation, alkoxylation, and amination with high chemoselectivity. In addition to batch reactions, an electrophotocatalytic recirculating flow process is demonstrated, enabling the conversion of benzene to phenol on a gram scale.

Entities: Chemical

Keywords: alkoxylation; amination; electrophotocatalysis; hydroxylation; photochemistry

Mesh：

Substances：

Year: 2021 PMID： 33661562 PMCID： PMC8099024 DOI： 10.1002/anie.202100222

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

35 in total

1. Organic synthetic transformations using organic dyes as photoredox catalysts.

Authors: Shunichi Fukuzumi; Kei Ohkubo
Journal: Org Biomol Chem Date: 2014-07-02 Impact factor: 3.876

2. Manganese-Catalyzed Oxidative Azidation of C(sp³)-H Bonds under Electrophotocatalytic Conditions.

Authors: Linbin Niu; Chongyu Jiang; Yuwei Liang; Dingdong Liu; Faxiang Bu; Renyi Shi; Hong Chen; Abhishek Dutta Chowdhury; Aiwen Lei
Journal: J Am Chem Soc Date: 2020-09-29 Impact factor: 15.419

3. Photoelectrochemical C-H Alkylation of Heteroarenes with Organotrifluoroborates.

Authors: Hong Yan; Zhong-Wei Hou; Hai-Chao Xu
Journal: Angew Chem Int Ed Engl Date: 2019-02-04 Impact factor: 15.336

4. A one-step conversion of benzene to phenol with a palladium membrane.

Authors: Shu-ichi Niwa Si; Muthusamy Eswaramoorthy; Jalajakumari Nair; Anuj Raj; Naotsugu Itoh; Hiroshi Shoji; Takemi Namba; Fujio Mizukami
Journal: Science Date: 2002-01-04 Impact factor: 47.728

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

Authors: He Huang; Tristan H Lambert
Journal: Angew Chem Int Ed Engl Date: 2019-11-22 Impact factor: 15.336

6. Reductive Electrophotocatalysis: Merging Electricity and Light To Achieve Extreme Reduction Potentials.

Authors: Hyunwoo Kim; Hyungjun Kim; Tristan H Lambert; Song Lin
Journal: J Am Chem Soc Date: 2020-01-17 Impact factor: 15.419

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

Authors: He Huang; Zack M Strater; Tristan H Lambert
Journal: J Am Chem Soc Date: 2020-01-14 Impact factor: 15.419

8. Photocatalytic oxidation of benzene to phenol using dioxygen as an oxygen source and water as an electron source in the presence of a cobalt catalyst.

Authors: Ji Won Han; Jieun Jung; Yong-Min Lee; Wonwoo Nam; Shunichi Fukuzumi
Journal: Chem Sci Date: 2017-08-21 Impact factor: 9.825

Review 9. Synthetic Photoelectrochemistry.

Authors: Joshua P Barham; Burkhard König
Journal: Angew Chem Int Ed Engl Date: 2020-04-06 Impact factor: 15.336

10. Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors: Stefano Crespi; Maurizio Fagnoni
Journal: Chem Rev Date: 2020-08-06 Impact factor: 60.622

7 in total

Review 1. 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

Review 7. Synthetic Molecular Photoelectrochemistry: New Frontiers in Synthetic Applications, Mechanistic Insights and Scalability.

Authors: Shangze Wu; Jaspreet Kaur; Tobias A Karl; Xianhai Tian; Joshua P Barham
Journal: Angew Chem Int Ed Engl Date: 2022-02-09 Impact factor: 16.823