C-H Trifluoromethylthiolation of aldehyde hydrazones

Victor Levet; Balu Ramesh; Congyang Wang; Tatiana Besset

doi:10.3762/bjoc.20.242

C-H Trifluoromethylthiolation of aldehyde hydrazones

Beilstein J Org Chem. 2024 Nov 12:20:2883-2890. doi: 10.3762/bjoc.20.242. eCollection 2024.

Authors

Victor Levet¹, Balu Ramesh¹, Congyang Wang², Tatiana Besset¹

Affiliations

¹ INSA Rouen Normandie, Univ Rouen Normandie, CNRS, Normandie Univ, COBRA UMR 6014, INC3M FR 3038, F-76000 Rouen, France.
² Beijing National Laboratory for Molecular Sciences CAS key Laboratory of Molecular Recognition and Function CAS Research/Education Center for Excellence in Molecular Sciences Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Abstract

The selective C-H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C-SCF₃ bond was achieved under oxidative and mild reaction conditions in the presence of the readily available AgSCF₃ salt via a one-pot sequential process (28 examples, up to 91% yield). Mechanistic investigations revealed that AgSCF₃ was the active species in the transformation.

Keywords: C–H bond functionalization; C–S bond formation; hydrazones; synthetic method; trifluoromethylthiolation.

Grants and funding

This work has been partially supported by University of Rouen Normandy, INSA Rouen Normandy, the Centre National de la Recherche Scientifique (CNRS), European Regional Development Fund (ERDF), Labex SynOrg (ANR-11-LABX-0029), Carnot Institute I2C, the graduate school for research XL-Chem (ANR-18-EURE-0020 XL CHEM), and Region Normandie. V.L. thanks the region Normandie for a doctoral fellowship. The French National Research Agency (ANR-21-CE07-0035-02 and ANR-22-CE92-0083) is gratefully acknowledged for generous financial support. R.B. thanks Normandy Region for a post-doctoral fellowship with the project NextFluoChem under the program «Normandie Recherche—Labels d’excellence» (n°23E02521).