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Literature DB >> 27936294

Disulfide-Catalyzed Visible-Light-Mediated Oxidative Cleavage of C=C Bonds and Evidence of an Olefin-Disulfide Charge-Transfer Complex.

Yuchao Deng^1,2,3, Xiao-Jing Wei⁴, Hui Wang¹, Yuhan Sun^1,2, Timothy Noël⁴, Xiao Wang^1,5.

Abstract

A photocatalytic method for the aerobic oxidative cleavage of C=C bonds has been developed. Electron-rich aromatic disulfides were employed as photocatalyst. Upon visible-light irradiation, typical mono- and multi-substituted aromatic olefins could be converted into ketones and aldehydes at ambient temperature. Experimental and computational studies suggest that a disulfide-olefin charge-transfer complex is possibly responsible for the unconventional dissociation of S-S bond under visible light.

Entities: Chemical

Keywords: disulfide catalysts; donor-acceptor complexes; olefin oxidation; organocatalysis; visible-light photocatalysis

Year: 2016 PMID： 27936294 DOI： 10.1002/anie.201607948

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

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Cited

8 in total

1. Visible-Light-Promoted C-S Cross-Coupling via Intermolecular Charge Transfer.

Authors: Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal: J Am Chem Soc Date: 2017-09-19 Impact factor: 15.419

2. Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited-State Intramolecular Proton-Transfer Photocycloaddition.

Authors: Wenyu Wang; Anthony Clay; Retheesh Krishnan; Neil J Lajkiewicz; Lauren E Brown; Jayaraman Sivaguru; John A Porco
Journal: Angew Chem Int Ed Engl Date: 2017-10-13 Impact factor: 15.336

3. Transition-metal-free synthesis of 3-sulfenylated chromones via KIO₃-catalyzed radical C(sp²)-H sulfenylation.

Authors: Yanhui Guo; Shanshan Zhong; Li Wei; Jie-Ping Wan
Journal: Beilstein J Org Chem Date: 2017-09-27 Impact factor: 2.883

Review 4. An overview on disulfide-catalyzed and -cocatalyzed photoreactions.

Authors: Yeersen Patehebieke
Journal: Beilstein J Org Chem Date: 2020-06-23 Impact factor: 2.883

5. Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen.

Authors: Tao Yu; Mingqing Guo; Simiaomiao Wen; Rongrong Zhao; Jinlong Wang; Yanli Sun; Qixing Liu; Haifeng Zhou
Journal: RSC Adv Date: 2021-04-14 Impact factor: 3.361

Disulfide-Catalyzed Visible-Light-Mediated Oxidative Cleavage of C=C Bonds and Evidence of an Olefin-Disulfide Charge-Transfer Complex.

1. Visible-Light-Promoted C-S Cross-Coupling via Intermolecular Charge Transfer.

2. Total Syntheses of the Isomeric Aglain Natural Products Foveoglin A and Perviridisin B: Selective Excited-State Intramolecular Proton-Transfer Photocycloaddition.

3. Transition-metal-free synthesis of 3-sulfenylated chromones via KIO₃-catalyzed radical C(sp²)-H sulfenylation.

Review 4. An overview on disulfide-catalyzed and -cocatalyzed photoreactions.

5. Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen.

6. Oxidative Cleavage of Alkenes by O₂ with a Non-Heme Manganese Catalyst.

7. Thiol-ene/oxidation tandem reaction under visible light photocatalysis: synthesis of alkyl sulfoxides.

8. The cumene/O₂ system: a very simple tool for the radical chain oxidation of some functional groups.