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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
Abstract : 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 Trifluoromethyl Fluorine Perfluoroketene dithioacetal Furan
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046201
Contributor : Madeleine Roux-Merlin Connect in order to contact the contributor
Submitted on : Friday, February 22, 2019 - 3:36:30 PM
Last modification on : Thursday, October 14, 2021 - 1:10:08 PM

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UNIROUEN | INSA-ROUEN | CNRS | COBRA | COMUE-NORMANDIE | URCA | ICMR | INC-CNRS | CAPSANTE | INSA-GROUPE | ENSICAEN | UNILEHAVRE | UNICAEN | U-PICARDIE

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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, Elsevier, 2016, 72 (43), pp.6807-6814. ⟨10.1016/j.tet.2016.09.009⟩. ⟨hal-02046201⟩

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