Cu-Catalyzed C(sp²−H)-Trifluoromethylation of Aldehyde Hydrazones with Langlois Reagent

Author

Jatin Mehta
Puspa Aryal
Prakash Reddy, Missouri University of Science and TechnologyFollow

Abstract

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.

Recommended Citation

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

Department(s)

Chemistry

Keywords and Phrases

Catalysis; Hydrazones; Langlois Reagent; Trifluoromethylation

International Standard Serial Number (ISSN)

1099-0690; 1434-193X

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2021 Wiley, All rights reserved.

Publication Date

08 Apr 2021