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Literature DB >> 31904939

Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity.

He Huang¹, Zack M Strater², Tristan H Lambert^1,2.

Abstract

The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

Entities: Chemical Disease Species

Year: 2020 PMID： 31904939 PMCID： PMC7251231 DOI： 10.1021/jacs.9b11472

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

32 in total

1. Chemistry. Adding aliphatic C-H bond oxidations to synthesis.

Authors: M Christina White
Journal: Science Date: 2012-02-17 Impact factor: 47.728

2. O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols.

Authors: Jenna L Jeffrey; Jack A Terrett; David W C MacMillan
Journal: Science Date: 2015-08-27 Impact factor: 47.728

3. Understanding hydrogen atom transfer: from bond strengths to Marcus theory.

Authors: James M Mayer
Journal: Acc Chem Res Date: 2010-10-26 Impact factor: 22.384

Review 4. Rings in drugs.

Authors: Richard D Taylor; Malcolm MacCoss; Alastair D G Lawson
Journal: J Med Chem Date: 2014-02-17 Impact factor: 7.446

5. 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

6. Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

Authors: Jian Jin; David W C MacMillan
Journal: Angew Chem Int Ed Engl Date: 2014-12-02 Impact factor: 15.336

7. Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis.

Authors: Anhua Hu; Jing-Jing Guo; Hui Pan; Zhiwei Zuo
Journal: Science Date: 2018-07-26 Impact factor: 47.728

8. Tuning reactivity and selectivity in hydrogen atom transfer from aliphatic C-H bonds to alkoxyl radicals: role of structural and medium effects.

Authors: Michela Salamone; Massimo Bietti
Journal: Acc Chem Res Date: 2015-11-06 Impact factor: 22.384

9. Direct arylation of strong aliphatic C-H bonds.

Authors: Ian B Perry; Thomas F Brewer; Patrick J Sarver; Danielle M Schultz; Daniel A DiRocco; David W C MacMillan
Journal: Nature Date: 2018-08-01 Impact factor: 49.962

Review 10. Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis.

Authors: Luca Capaldo; Davide Ravelli
Journal: European J Org Chem Date: 2017-03-02

19 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. A redox-active organic salt for safer Na-ion batteries.

Authors: Weixiao Ji; He Huang; Xiaoxiao Zhang; Dong Zheng; Tianyao Ding; Tristan H Lambert; Deyang Qu
Journal: Nano Energy Date: 2020-03-13 Impact factor: 17.881

Review 3. 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

Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity.

1. Chemistry. Adding aliphatic C-H bond oxidations to synthesis.

2. O-H hydrogen bonding promotes H-atom transfer from α C-H bonds for C-alkylation of alcohols.

3. Understanding hydrogen atom transfer: from bond strengths to Marcus theory.

Review 4. Rings in drugs.

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

6. Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

7. Selective functionalization of methane, ethane, and higher alkanes by cerium photocatalysis.

8. Tuning reactivity and selectivity in hydrogen atom transfer from aliphatic C-H bonds to alkoxyl radicals: role of structural and medium effects.

9. Direct arylation of strong aliphatic C-H bonds.

Review 10. Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis.

1. Electrophotocatalytic diamination of vicinal C-H bonds.

2. A redox-active organic salt for safer Na-ion batteries.

Review 3. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

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

5. Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins.

6. Electrophotocatalytic C-H Heterofunctionalization of Arenes.

Review 7. Oxidase reactions in photoredox catalysis.

8. Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity*.

9. C-H Amination via Electrophotocatalytic Ritter-type Reaction.

Review 10. Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.