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Angew Chem Int Ed Engl. 2015 Mar 2;54(10):3065-8. doi: 10.1002/anie.201410301. Epub 2015 Jan 22.

Dinuclear copper intermediates in copper(I)-catalyzed azide-alkyne cycloaddition directly observed by electrospray ionization mass spectrometry.

Author information

1
Dipartimento di Scienze Fisiche e Chimiche Università dell'Aquila, Via Vetoio, Coppito, 67100 L'Aquila (Italy).

Abstract

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.

KEYWORDS:

CuAAC reaction; click chemistry; dicopper complexes; mass spectrometry; reactive intermediates

PMID:
25614295
DOI:
10.1002/anie.201410301

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