Literature DB >> 28402669

N-Trifluoromethylation of Nitrosoarenes with Sodium Triflinate.

Angela van der Werf1, Matic Hribersek1, Nicklas Selander1.   

Abstract

A highly efficient N-trifluoromethylation of nitrosoarenes is reported. The inexpensive and convenient Langlois reagent (sodium triflinate) is employed as a CF3-radical source in combination with a copper catalyst and an oxidant. N-Trifluoromethylated hydroxylamines are obtained in high yields within 1 h at room temperature. The addition of hydroquinone was found to be instrumental to prevent the formation of side products. The method is high-yielding, is scalable, and displays a high functional group tolerance.

Entities:  

Year:  2017        PMID: 28402669     DOI: 10.1021/acs.orglett.7b00908

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


  6 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

2.  Synthesis of N-trifluoromethyl amides from carboxylic acids.

Authors:  Jianbo Liu; Matthew F L Parker; Sinan Wang; Robert R Flavell; F Dean Toste; David M Wilson
Journal:  Chem       Date:  2021-08-03       Impact factor: 25.832

3.  Copper(i) reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.

Authors:  Qing Wang; Peng Shi; Runsheng Zeng
Journal:  RSC Adv       Date:  2018-07-19       Impact factor: 4.036

4.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na.

Authors:  Hélène Guyon; Hélène Chachignon; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2017-12-19       Impact factor: 2.883

5.  Cu and Hydroquinone for the Trifluoromethylation of Unprotected Phenols.

Authors:  Jakob Pletz; Christoph Koeberl; Michael Fuchs; Oliver Steiner; Walter Goessler; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2018-10-08

6.  Synthesis of Fluorinated Amide Derivatives via a Radical N-Perfluoroalkylation-Defluorination Pathway.

Authors:  Zhiyao Zheng; Angela van der Werf; Marie Deliaval; Nicklas Selander
Journal:  Org Lett       Date:  2020-03-25       Impact factor: 6.005

  6 in total

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