Straightforward synthesis of tri- and tetra-substituted 3-trifluoromethylfurans by heterocyclization reaction of perfluoroketene dithioacetals

Clément de Saint Jores (1) , Ivan Mukan (1, 2) , Tatyana Yegorova (1, 2) , Dominique Harakat (3) , J.-P. Bouillon (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 Taras Shevchenko National University of Kyiv
3 ICMR - Institut de Chimie Moléculaire de Reims - UMR 7312

Various 2-ethylsulfanyl-3-trifluoromethylfurans were obtained, in moderate to good yields, using a two-step procedure, from perfluoroketene dithioacetals as starting materials. Reaction tolerated a large variety of substituents on the furan nucleus. Mechanism of cyclization was also proposed based on the electronic properties of aryl and heteroaryl substituents.

Keywords: Heterocycle; Furan; Perfluoroketene dithioacetal; Fluorine; Trifluoromethyl

Domains: Chemical Sciences

Clément de Saint Jores, Ivan Mukan, Tatyana Yegorova, Dominique Harakat, J.-P. Bouillon. Straightforward synthesis of tri- and tetra-substituted 3-trifluoromethylfurans by heterocyclization reaction of perfluoroketene dithioacetals. Tetrahedron, 2016, 72 (43), pp.6807-6814. ⟨10.1016/j.tet.2016.09.009⟩. ⟨hal-02046201⟩