Literature DB >> 30964599

Visible-Light Photoredox-Catalyzed and Copper-Promoted Trifluoromethoxylation of Arenediazonium Tetrafluoroborates.

Shaoqiang Yang1, Miao Chen1, Pingping Tang1.   

Abstract

We report the development of photoredox-catalyzed and copper-promoted trifluoromethoxylation of arenediazonium tetrafluoroborates, with trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxylation reagent. This new method takes advantage of visible-light photoredox catalysis to generate the aryl radical under mild conditions, combined with copper-promoted selective trifluoromethoxylation. The reaction is scalable, tolerates a wide range of functional groups, and proceeds regioselectively under mild reaction conditions. Furthermore, mechanistic studies suggested that a Cs[Cu(OCF3 )2 ] intermediate might be generated during the reaction.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; photoredox catalysis; synthetic methods; trifluoromethoxylation; trifluoromethyl arylsulfonate

Year:  2019        PMID: 30964599     DOI: 10.1002/anie.201901447

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


  4 in total

1.  Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

Authors:  Johnny W Lee; Sanghyun Lim; Daniel N Maienshein; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-24       Impact factor: 15.336

2.  Trifluoromethyl Nonaflate: A Practical Trifluoromethoxylating Reagent and its Application to the Regio- and Stereoselective Synthesis of Trifluoromethoxylated Alkenes.

Authors:  Zhichao Lu; Tatsuya Kumon; Gerald B Hammond; Teruo Umemoto
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

3.  Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow.

Authors:  Alexander V Nyuchev; Ting Wan; Borja Cendón; Carlo Sambiagio; Job J C Struijs; Michelle Ho; Moisés Gulías; Ying Wang; Timothy Noël
Journal:  Beilstein J Org Chem       Date:  2020-06-15       Impact factor: 2.883

4.  Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers.

Authors:  Michał Jakubczyk; Satenik Mkrtchyan; Mohanad Shkoor; Suneel Lanka; Šimon Budzák; Miroslav Iliaš; Marek Skoršepa; Viktor O Iaroshenko
Journal:  J Am Chem Soc       Date:  2022-06-02       Impact factor: 16.383

  4 in total

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