Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions

Arnaud Boreux (1, 2) , Aubin Lambion (2) , Dominic Campeau (3) , Marina Sanita (3) , Ruben Coronel (3) , Olivier Riant (2) , Fabien Gagosz (1, 3)

1 DCSO - Laboratoire de synthèse organique
2 IMCN - Institut de la matière condensée et des nanosciences / Institute of Condensed Matter and Nanosciences
3 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall

The synthesis of fluorinated synthetic intermediates has become a field of intense research in organic chemistry. In this article, we report the application of a gold-catalyzed rearrangement to the synthesis of β-trifluoromethylated α,β-unsaturated ketones. The scope of the reaction, as well as the valorization of the products in subsequent transformations has been investigated. This study allowed for the preparation of various CF3-substituted enones and fluorinated Diels-Alder adducts from easily accessible starting materials.

Keywords: Gold catalysis; α; β-unsaturated ketones; Trifluoromethyl group; Propargylic acetates

Domains: Chemical Sciences; Organic chemistry

Arnaud Boreux, Aubin Lambion, Dominic Campeau, Marina Sanita, Ruben Coronel, et al.. Gold-catalyzed synthesis of β-trifluoromethylated α,β-unsaturated ketones from CF3-substituted propargylic carboxylates and their reactivity in Diels-Alder reactions. Tetrahedron, 2018, 74 (38), pp.5232-5239. ⟨10.1016/j.tet.2018.05.054⟩. ⟨hal-02096386⟩