Literature DB >> 26356627

Silver(I)-Catalyzed N-Trifluoroethylation of Anilines and O-Trifluoroethylation of Amides with 2,2,2-Trifluorodiazoethane.

Haiqing Luo1,2, Guojiao Wu1, Yan Zhang1, Jianbo Wang3.   

Abstract

A straightforward N-trifluoroethylation of anilines has been developed based on silver-catalyzed N-H insertions with 2,2,2-trifluorodiazoethane (CF3CHN2). Mechanistically, the reaction is proposed to involve migratory insertion of a silver carbene as the key step. In contrast, when amides are employed as the substrates under similar reaction conditions, O-trifluoroethylation occurs to afford trifluoroethyl imidates.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amides; aniline; carbenes; diazo compounds; silver

Year:  2015        PMID： 26356627     DOI： 10.1002/anie.201507219

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


  8 in total

1.  Enantiodivergent α-Amino C-H Fluoroalkylation Catalyzed by Engineered Cytochrome P450s.

Authors:  Juner Zhang; Xiongyi Huang; Ruijie K Zhang; Frances H Arnold
Journal:  J Am Chem Soc       Date:  2019-06-12       Impact factor: 15.419

2.  Aryl amination using ligand-free Ni(II) salts and photoredox catalysis.

Authors:  Emily B Corcoran; Michael T Pirnot; Shishi Lin; Spencer D Dreher; Daniel A DiRocco; Ian W Davies; Stephen L Buchwald; David W C MacMillan
Journal:  Science       Date:  2016-06-23       Impact factor: 47.728

3.  A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid.

Authors:  Keith G Andrews; Radmila Faizova; Ross M Denton
Journal:  Nat Commun       Date:  2017-06-26       Impact factor: 14.919

4.  Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.

Authors:  Xinyu Zhang; Zhaohong Liu; Xiangyu Yang; Yuanqing Dong; Matteo Virelli; Giuseppe Zanoni; Edward A Anderson; Xihe Bi
Journal:  Nat Commun       Date:  2019-01-17       Impact factor: 14.919

5.  AgNTf2-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives.

Authors:  Ziping Cao; Jiekun Zhu; Li Liu; Yuanling Pang; Laijin Tian; Xuejun Sun; Xin Meng
Journal:  Beilstein J Org Chem       Date:  2019-11-04       Impact factor: 2.883

6.  Iron porphyrin-catalyzed N-trifluoroethylation of anilines with 2,2,2-trifluoroethylamine hydrochloride in aqueous solution.

Authors:  Shuang Ren; Guiming Xu; Yongjia Guo; Qiang Liu; Cancheng Guo
Journal:  RSC Adv       Date:  2021-06-07       Impact factor: 4.036

7.  Gold(I) α-Trifluoromethyl Carbenes: Synthesis, Characterization and Reactivity Studies.

Authors:  Mathilde Rigoulet; David Vesseur; Karinne Miqueu; Didier Bourissou
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-03       Impact factor: 16.823

8.  Silver-Catalyzed Regio- and Stereoselective Formal Carbene Insertion into Unstrained C-C σ-Bonds of 1,3-Dicarbonyls.

Authors:  Zhaohong Liu; Xinyu Zhang; Matteo Virelli; Giuseppe Zanoni; Edward A Anderson; Xihe Bi
Journal:  iScience       Date:  2018-09-18
  8 in total

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