Literature DB >> 24437369

Direct C-F bond formation using photoredox catalysis.

Montserrat Rueda-Becerril1, Olivier Mahé, Myriam Drouin, Marek B Majewski, Julian G West, Michael O Wolf, Glenn M Sammis, Jean-François Paquin.   

Abstract

We have developed the first example of a photoredox catalytic method for the formation of carbon-fluorine (C-F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the (3)MLCT (triplet metal-to-ligand charge transfer) state of Ru(bpy)3(2+) to Selectfluor. Not only does this represent a new reaction for photoredox catalysis, but the mild reaction conditions and use of visible light also make it a practical improvement over previously developed UV-mediated decarboxylative fluorinations.

Entities:  

Year:  2014        PMID: 24437369     DOI: 10.1021/ja412083f

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


  18 in total

1.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

2.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

Review 3.  Heterogeneous photocatalysis in flow chemical reactors.

Authors:  Christopher G Thomson; Ai-Lan Lee; Filipe Vilela
Journal:  Beilstein J Org Chem       Date:  2020-06-26       Impact factor: 2.883

4.  Photocatalytic Aminodecarboxylation of Carboxylic Acids.

Authors:  Simon B Lang; Kaitie C Cartwright; Richard S Welter; Theresa M Locascio; Jon A Tunge
Journal:  European J Org Chem       Date:  2016-06-19

5.  Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

Authors:  Sandrine Ventre; Filip R Petronijevic; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-04-27       Impact factor: 15.419

6.  Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.

Authors:  Lingling Chu; Jeffrey M Lipshultz; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-26       Impact factor: 15.336

7.  Decarboxylative Halogenation of Organic Compounds.

Authors:  Andrii Varenikov; Evgeny Shapiro; Mark Gandelman
Journal:  Chem Rev       Date:  2020-11-17       Impact factor: 60.622

Review 8.  Oxidase reactions in photoredox catalysis.

Authors:  Nicholas L Reed; Tehshik P Yoon
Journal:  Chem Soc Rev       Date:  2021-01-25       Impact factor: 54.564

9.  Metal-free electrochemical fluorodecarboxylation of aryloxyacetic acids to fluoromethyl aryl ethers.

Authors:  Michael Berger; John D Herszman; Yuji Kurimoto; Goswinus H M de Kruijff; Aaron Schüll; Sven Ruf; Siegfried R Waldvogel
Journal:  Chem Sci       Date:  2020-06-01       Impact factor: 9.825

10.  Installing amino acids and peptides on N-heterocycles under visible-light assistance.

Authors:  Yunhe Jin; Min Jiang; Hui Wang; Hua Fu
Journal:  Sci Rep       Date:  2016-02-02       Impact factor: 4.379

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