Cu-Catalyzed C(sp²−H)-Trifluoromethylation of Aldehyde Hydrazones with Langlois Reagent
The C(sp2−H)-trifluoromethylation of hydrazones would give access to the α-trifluoromethylated hydrazones that can serve as intermediates in the synthesis of pharmaceutically interesting fluorinated compounds. Herein, we demonstrate the Cu-catalyzed C(sp2−H)-trifluoromethylation of the aldehyde hydrazones using the readily available and cost effective Langlois reagent (sodium trifluoromethanesulfinate). This reaction is broadly applicable to a series of aromatic aldehyde N-aminomorpholine hydrazones to give the corresponding C(sp2)-trifluoromethyl hydrazones in moderate to high yields. The reaction generally tolerates a series of electron-releasing as well as electron-withdrawing substituents on the aromatic ring.
J. Mehta et al., "Cu-Catalyzed C(sp²−H)-Trifluoromethylation of Aldehyde Hydrazones with Langlois Reagent," European Journal of Organic Chemistry, vol. 2021, no. 13, pp. 2018 - 2024, Wiley, Apr 2021.
The definitive version is available at https://doi.org/10.1002/ejoc.202100205
Keywords and Phrases
Catalysis; Hydrazones; Langlois Reagent; Trifluoromethylation
International Standard Serial Number (ISSN)
Article - Journal
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08 Apr 2021