Literature DB >> 19835360

Toward the synthesis of the rare N-(trifluoromethyl)amides and the N-(difluoromethylene)-N-(trifluoromethyl)amines [RN(CF3)CF2R'] using BrF3.

Youlia Hagooly1, Julia Gatenyo, Aviv Hagooly, Shlomo Rozen.   

Abstract

A synthesis of a wide range of different aliphatic, aromatic, and heterocyclic N-(trifluoromethyl)amides along with aromatic N-(difluoromethylene)-N-(trifluoromethyl)amine derivatives has been developed. The starting materials are the easily available isothiocyanates, and the fluorinating reagent is the commercially available bromine trifluoride. The reaction is performed under mild conditions, and the fluorinated amides and amines are produced in moderate to high yields.

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Year:  2009        PMID: 19835360     DOI: 10.1021/jo901560b

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  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

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.  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

  3 in total

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