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Literature DB >> 33949852

Electrophotocatalytic Acetoxyhydroxylation of Aryl Olefins.

Abstract

A method for the acetoxyhydroxylation of olefins with syn stereoselectivity under electrophotocatalytic conditions is described. The procedure uses a trisaminocyclopropenium (TAC) ion catalyst with visible light irradiation under a controlled electrochemical potential to convert aryl olefins to the corresponding glycol monoesters with high chemo- and diastereoselectivity. This reaction can be performed in batch or in flow, enabling multigram synthesis of the monoester products.

Entities: Chemical

Mesh：

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Year: 2021 PMID： 33949852 PMCID： PMC8145777 DOI： 10.1021/jacs.1c01967

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

38 in total

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Authors: M Costas; A K Tipton; K Chen; D H Jo; L Que
Journal: J Am Chem Soc Date: 2001-07-11 Impact factor: 15.419

2. Chemical and Electrochemical Asymmetric Dihydroxylation of Olefins in I(2)-K(2)CO(3)-K(2)OsO(2)(OH)(4) and I(2)-K(3)PO(4)/K(2)HPO(4)-K(2)OsO(2)(OH)(4) Systems with Sharpless' Ligand.

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Journal: J Org Chem Date: 1996-05-03 Impact factor: 4.354

Review 3. Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment.

Authors: Dario Cambié; Cecilia Bottecchia; Natan J W Straathof; Volker Hessel; Timothy Noël
Journal: Chem Rev Date: 2016-03-03 Impact factor: 60.622

4. Electroorganic Synthesis under Flow Conditions.

Authors: Mohamed Elsherbini; Thomas Wirth
Journal: Acc Chem Res Date: 2019-11-06 Impact factor: 22.384

5. Electrocatalytic oxidative cleavage of electron-deficient substituted stilbenes in acetonitrile-water employing a new high oxidation potential electrocatalyst. An electrochemical equivalent of ozonolysis.

Authors: Xin Wu; Anthony P Davis; Albert J Fry
Journal: Org Lett Date: 2007-11-30 Impact factor: 6.005

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. Electrophotocatalytic C-H Heterofunctionalization of Arenes.

Authors: He Huang; Tristan H Lambert
Journal: Angew Chem Int Ed Engl Date: 2021-04-12 Impact factor: 15.336

9. Photoelectrocatalytic Arene C-H Amination.

Authors: Lei Zhang; Laurent Liardet; Jingshan Luo; Dan Ren; Michael Grätzel; Xile Hu
Journal: Nat Catal Date: 2019-02-18

Review 10. New Redox Strategies in Organic Synthesis by Means of Electrochemistry and Photochemistry.

Authors: Jinjian Liu; Lingxiang Lu; Devin Wood; Song Lin
Journal: ACS Cent Sci Date: 2020-07-16 Impact factor: 14.553

3 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

2. Photophysics of Perylene Diimide Dianions and Their Application in Photoredox Catalysis.

Authors: Han Li; Oliver S Wenger
Journal: Angew Chem Int Ed Engl Date: 2021-12-20 Impact factor: 16.823

3. Catalytic Synthesis of Cyclopropenium Cations with Rh-Carbynoids.

Authors: Hang-Fei Tu; Aliénor Jeandin; Marcos G Suero
Journal: J Am Chem Soc Date: 2022-09-08 Impact factor: 16.383

3 in total