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Dinuclear Copper Intermediates in Copper(I)‐Catalyzed Azide–Alkyne Cycloaddition Directly Observed by Electrospray Ionization Mass Spectrometry
Author(s) -
Iacobucci Claudio,
Reale Samantha,
Gal JeanFrançois,
De Angelis Francesco
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410301
Subject(s) - electrospray ionization , chemistry , copper , cycloaddition , mass spectrometry , alkyne , catalysis , azide , catalytic cycle , electrospray , combinatorial chemistry , reaction mechanism , photochemistry , organic chemistry , chromatography
The mechanism of the CuAAC reaction has been investigated by electrospray ionization mass spectrometry (ESI‐MS) using a combination of the neutral reactant approach and the ion‐tagging strategy. Under these conditions, for the first time, putative dinuclear copper intermediates were fished out and characterized by ESI(+)‐MS/MS. New insight into the CuAAC reaction mechanisms is provided and a catalytic cycle is proposed.