Literature DB >> 23957499

Cupration of C2F5H: isolation, structure, and synthetic applications of [K(DMF)2][(t-BuO)Cu(C2F5)]. Highly efficient pentafluoroethylation of unactivated aryl bromides.

Anton Lishchynskyi1, Vladimir V Grushin.   

Abstract

Pentafluoroethane, C2F5H (HFC-125), is smoothly cuprated with preisolated or in situ-generated [K(DMF)][(t-BuO)2Cu] to give [K(DMF)2][(t-BuO)Cu(C2F5)] (1) in nearly quantitative yield. Complex 1 has been isolated, structurally characterized, and demonstrated to be an exceedingly versatile pentafluoroethylating reagent for a variety of substrates, including unactivated aryl bromides.

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Year:  2013        PMID: 23957499     DOI: 10.1021/ja407017j

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


  6 in total

1.  Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

Authors:  Sophie I Arlow; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-01       Impact factor: 15.336

2.  Metallaphotoredox Perfluoroalkylation of Organobromides.

Authors:  Xiangbo Zhao; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2020-11-09       Impact factor: 15.419

Review 3.  Repurposing of F-gases: challenges and opportunities in fluorine chemistry.

Authors:  Daniel J Sheldon; Mark R Crimmin
Journal:  Chem Soc Rev       Date:  2022-06-20       Impact factor: 60.615

Review 4.  Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F).

Authors:  Louise Ruyet; Tatiana Besset
Journal:  Beilstein J Org Chem       Date:  2020-05-18       Impact factor: 2.883

5.  Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols.

Authors:  Armin Ariamajd; Nils J Gerwien; Benjamin Schwabe; Stefan Dix; Matthew N Hopkinson
Journal:  Beilstein J Org Chem       Date:  2021-01-08       Impact factor: 2.883

6.  Regio- and Stereoselective Radical Perfluoroalkyltriflation of Alkynes Using Phenyl(perfluoroalkyl)iodonium Triflates.

Authors:  Xi Wang; Armido Studer
Journal:  Org Lett       Date:  2017-05-18       Impact factor: 6.005

  6 in total

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