Literature DB >> 25611040

Iron-catalyzed trifluoromethylation of enamide.

Romain Rey-Rodriguez1, Pascal Retailleau, Pascal Bonnet, Isabelle Gillaizeau.   

Abstract

Herein the first example of the iron(II)-catalyzed trifluoromethylation of enamide using mild and simple reaction conditions is reported. The method is cost-effective and uses the easy-to-handle Togni's reagent as the electrophilic CF3 source. This transformation is totally regioselective at the C3 position of enamides and exhibits broad substrate scope, good functional group tolerance and thus demonstrates its useful application in a late-stage fluorination strategy.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH functionalization; Togni’s reagent; iron-catalyzed reactions; synthetic methods; trifluoromethylation

Mesh:

Substances:

Year:  2015        PMID: 25611040     DOI: 10.1002/chem.201406333

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  Metal-free oxidative trifluoromethylation of indoles with CF3SO2Na on the C2 position.

Authors:  Jiao-Jiao Xie; Zhi-Qing Wang; Guo-Fang Jiang
Journal:  RSC Adv       Date:  2019-10-30       Impact factor: 4.036

Review 2.  Recent advances in direct trifluoromethylation of olefinic C-H bonds.

Authors:  Cao Yang; Akbar Hassanpour; Khatereh Ghorbanpour; Shahrzad Abdolmohammadi; Esmail Vessally
Journal:  RSC Adv       Date:  2019-09-03       Impact factor: 4.036

3.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors:  Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

4.  An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes.

Authors:  Vasiliy M Muzalevskiy; Zoia A Sizova; Vladimir T Abaev; Valentine G Nenajdenko
Journal:  Molecules       Date:  2021-12-04       Impact factor: 4.411

5.  Synthesis of trifluoromethyl-containing isoindolinones from tertiary enamides via a cascade radical addition and cyclization process.

Authors:  Hui Yu; Mingdong Jiao; Xiaowei Fang; Pengfei Xuan
Journal:  RSC Adv       Date:  2018-07-03       Impact factor: 3.361

6.  Synthesis of FeIII and FeIV Cyanide Complexes Using Hypervalent Iodine Reagents as Cyano-Transfer One-Electron Oxidants.

Authors:  Charafa Souilah; Sergio A V Jannuzzi; Derya Demirbas; Sergei Ivlev; Marcel Swart; Serena DeBeer; Alicia Casitas
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-29       Impact factor: 16.823

Review 7.  Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis.

Authors:  Gwendal Grelier; Benjamin Darses; Philippe Dauban
Journal:  Beilstein J Org Chem       Date:  2018-06-21       Impact factor: 2.883

  7 in total

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