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Literature DB >> 25144336

A continuous-flow protocol for light-induced benzylic fluorinations.

David Cantillo¹, Oscar de Frutos, Juan A Rincón, Carlos Mateos, C Oliver Kappe.

Abstract

A continuous-flow protocol for the light-induced fluorination of benzylic compounds is presented. The procedure uses Selectfluor as the fluorine source and xanthone as an inexpensive and commercially available photoorganocatalyst. The flow photoreactor is based on transparent fluorinated ethylene propylene tubing and a household compact fluorescent lamp. The combination of xanthone with black-light irradiation results in very efficient fluorination. Good to excellent isolated yields were obtained for a variety of substrates bearing different functional groups applying residence times below 30 min.

Entities: Chemical

Year: 2014 PMID： 25144336 DOI： 10.1021/jo5016757

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

12 in total

1. A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist.

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Journal: Angew Chem Int Ed Engl Date: 2015-10-16 Impact factor: 15.336

2. Natural products as inspiration for the development of new synthetic methods.

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3. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

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4. Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Brønsted Base.

Authors: Joshua A Buss; Aristidis Vasilopoulos; Dung L Golden; Shannon S Stahl
Journal: Org Lett Date: 2020-07-29 Impact factor: 6.005

Review 9. 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

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

Authors: Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal: Chem Rev Date: 2021-08-06 Impact factor: 60.622

A continuous-flow protocol for light-induced benzylic fluorinations.

1. A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist.

2. Natural products as inspiration for the development of new synthetic methods.

3. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

4. Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Brønsted Base.

5. The past, present, and future of the Yang reaction.

6. Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations.

7. Ketones as directing groups in photocatalytic sp³ C-H fluorination.

Review 8. Photosensitized direct C-H fluorination and trifluoromethylation in organic synthesis.

Review 9. Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis.

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