CuAAC Click Reactions in the Gas Phase: Unveiling the Reactivity of Bis-Copper Intermediates

Abstract : Copper-catalysed azide alkyne cycloaddition (CuAAC) has been considered a breakthrough transformation over the last 15 years. Its debated mechanism arouses continuously growing interest. By means of a mass spectrometer modified ad hoc, the entire catalytic cycle of CuAAC reaction has been investigated in the gas phase. Ion-molecule reactions were performed inside the mass spectrometer to reproduce step-by-step, at a molecular level, the complete catalytic cycle of the click reaction. We successfully challenged the reactivity of elusive mono- and bis-copper intermediates by ion-molecule reactions leading to the production of mass-characterized triazole products, paving the way for detailed energetic studies to be performed in the gas phase. The structures of the relevant species, calculated at a DFT level, helped rationalise our experimental results.
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Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22 (52), pp.18690 - 18694. 〈http://onlinelibrary.wiley.com/doi/10.1002/chem.201603518/abstract〉. 〈10.1002/chem.201603518〉
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http://hal.univ-brest.fr/hal-01539212
Contributeur : Nicolas Renard <>
Soumis le : mercredi 14 juin 2017 - 15:57:25
Dernière modification le : jeudi 11 janvier 2018 - 06:17:06

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Claudio Iacobucci, Alexandre Lebon, Francesco De Angelis, Antony Memboeuf. CuAAC Click Reactions in the Gas Phase: Unveiling the Reactivity of Bis-Copper Intermediates. Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22 (52), pp.18690 - 18694. 〈http://onlinelibrary.wiley.com/doi/10.1002/chem.201603518/abstract〉. 〈10.1002/chem.201603518〉. 〈hal-01539212〉

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