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Ortho -Functionalized Aryltetrazines by Direct Palladium-Catalyzed C−H Halogenation: Application to Fast Electrophilic Fluorination Reactions

Abstract : A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precursors). It gives access to ortho-functionalized aryltetrazines which are difficult to obtain by classical Pinner-like syntheses.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01399085
Contributeur : Icmub - Université de Bourgogne <>
Soumis le : vendredi 18 novembre 2016 - 12:26:08
Dernière modification le : dimanche 23 juin 2019 - 11:00:03

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Christelle Testa, Élodie Gigot, Semra Genc, Richard Decréau, Julien Roger, et al.. Ortho -Functionalized Aryltetrazines by Direct Palladium-Catalyzed C−H Halogenation: Application to Fast Electrophilic Fluorination Reactions. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2016, 55 (18), pp.5555 - 5559. ⟨10.1002/anie.201601082⟩. ⟨hal-01399085⟩

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