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- Title
CuAAC Click Reactions in the Gas Phase: Unveiling the Reactivity of Bis-Copper Intermediates.
- Authors
Iacobucci, Claudio; Lebon, Alexandre; De Angelis, Francesco; Memboeuf, Antony
- 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.
- Subjects
GAS phase reactions; INTERMEDIATES (Chemistry); COPPER; ION-molecule collisions; RING formation (Chemistry); MASS spectrometers
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 52, p18690
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201603518