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Literature DB >> 33596084

Photocatalyst-Free, Visible-Light-Mediated C(sp³)-H Arylation of Amides via a Solvent-Caged EDA Complex.

Jaspreet Kaur¹, Ahmed Shahin^1,2, Joshua P Barham¹.

Abstract

A photocatalyst-free and mild visible light photochemical procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)-H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction taking place in a solvent cage holding components in a close proximity.

Entities: Chemical Species

Year: 2021 PMID： 33596084 DOI： 10.1021/acs.orglett.1c00132

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

4 in total

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

Authors: Ling Zhang; Youtian Fu; Yi Shen; Chengyu Liu; Maolin Sun; Ruihua Cheng; Weiping Zhu; Xuhong Qian; Yueyue Ma; Jinxing Ye
Journal: Nat Commun Date: 2022-07-16 Impact factor: 17.694

2. Photocatalytic C-H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow.

Authors: Zhenghui Wen; Ting Wan; Arjun Vijeta; Carla Casadevall; Laura Buglioni; Erwin Reisner; Timothy Noël
Journal: ChemSusChem Date: 2021-10-22 Impact factor: 9.140

3. An organophotocatalytic late-stage N-CH₃ oxidation of trialkylamines to N-formamides with O₂ in continuous flow.

Authors: Mark John P Mandigma; Jonas Žurauskas; Callum I MacGregor; Lee J Edwards; Ahmed Shahin; Ludwig d'Heureuse; Philip Yip; David J S Birch; Thomas Gruber; Jörg Heilmann; Matthew P John; Joshua P Barham
Journal: Chem Sci Date: 2021-12-28 Impact factor: 9.825

4. Electrochemical Friedel-Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate.

Authors: Hisanori Senboku; Mizuki Hayama; Hidetoshi Matsuno
Journal: Beilstein J Org Chem Date: 2022-08-18 Impact factor: 2.544

4 in total

Photocatalyst-Free, Visible-Light-Mediated C(sp3)-H Arylation of Amides via a Solvent-Caged EDA Complex.

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

2. Photocatalytic C-H Azolation of Arenes Using Heterogeneous Carbon Nitride in Batch and Flow.

3. An organophotocatalytic late-stage N-CH3 oxidation of trialkylamines to N-formamides with O2 in continuous flow.

4. Electrochemical Friedel-Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate.

Photocatalyst-Free, Visible-Light-Mediated C(sp³)-H Arylation of Amides via a Solvent-Caged EDA Complex.

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

3. An organophotocatalytic late-stage N-CH₃ oxidation of trialkylamines to N-formamides with O₂ in continuous flow.