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Issue 6, 2018
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Chemoselective direct reductive trifluoromethylation of amides: a flexible access to functionalized α-trifluoromethylamines

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Abstract

The direct transformation of amides is an emerging area in organic synthesis. Starting from common secondary amides, a novel and flexible approach to α-trifluoromethylamines is described. This one-pot method consists of the in situ activation of amides with triflic anhydride (Tf2O), partial reduction with 1,1,3,3-tetramethyldisiloxane (TMDS), and nucleophilic trifluoromethylation with trifluoromethyltrimethylsilane (TMSCF3). Thanks to the mild conditions, the reaction exhibited high chemoselectivity and good functional group tolerance.

Graphical abstract: Chemoselective direct reductive trifluoromethylation of amides: a flexible access to functionalized α-trifluoromethylamines

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Publication details

The article was received on 17 Nov 2017, accepted on 11 Dec 2017 and first published on 12 Dec 2017


Article type: Research Article
DOI: 10.1039/C7QO01031A
Citation: Org. Chem. Front., 2018,5, 943-947
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    Chemoselective direct reductive trifluoromethylation of amides: a flexible access to functionalized α-trifluoromethylamines

    H. Chen, J. Ye and P. Huang, Org. Chem. Front., 2018, 5, 943
    DOI: 10.1039/C7QO01031A

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