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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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Submitted on : Wednesday, June 14, 2017 - 3:57:25 PM
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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, 2016, 22 (52), pp.18690 - 18694. ⟨10.1002/chem.201603518⟩. ⟨hal-01539212⟩



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