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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201410301
Subject(s) - electrospray ionization , copper , chemistry , mass spectrometry , cycloaddition , alkyne , azide , catalysis , 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.