Literature DB >> 22615188

Direct electrophilic N-trifluoromethylation of azoles by a hypervalent iodine reagent.

Katrin Niedermann1, Natalja Früh, Remo Senn, Barbara Czarniecki, René Verel, Antonio Togni.   

Abstract

Effective CF(3) transfer: Various electron-rich nitrogen heterocycles (pyrazoles, triazoles, and tetrazoles) can be directly N-trifluoromethylated by a hypervalent iodine reagent in an efficient manner. The optimized procedure, which includes an in situ silylation of the substrate followed by an acid-catalyzed CF(3) transfer, provides ready access to a series of new and previously challenging or inaccessible NCF(3) compounds.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Mesh:

Substances:

Year:  2012        PMID: 22615188     DOI: 10.1002/anie.201201572

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


  5 in total

1.  Structural reevaluation of the electrophilic hypervalent iodine reagent for trifluoromethylthiolation supported by the crystalline sponge method for X-ray analysis.

Authors:  Ekaterina V Vinogradova; Peter Müller; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

2.  Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me4 N)SCF3.

Authors:  Thomas Scattolin; Kristina Deckers; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-09       Impact factor: 15.336

3.  Cation versus Radical: Studies on the C/O Regioselectivity in Electrophilic Tri-, Di- and Monofluoromethylations of β-Ketoesters.

Authors:  Yu-Dong Yang; Xu Lu; Guokai Liu; Etsuko Tokunaga; Seiji Tsuzuki; Norio Shibata
Journal:  ChemistryOpen       Date:  2012-10-11       Impact factor: 2.911

4.  Isolation and Reactivity of Trifluoromethyl Iodonium Salts.

Authors:  Johnathan N Brantley; Andrew V Samant; F Dean Toste
Journal:  ACS Cent Sci       Date:  2016-05-13       Impact factor: 14.553

5.  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

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.