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Real-Time Monitoring of a Cobalt-Mediated One-Pot Transition Metal Catalyzed Multicomponent Reaction

preprint
submitted on 09.03.2020 and posted on 10.03.2020 by Antonio Crotti, Daniel Previdi, Paulo Donate, J Scott McIndoe
In this paper, pressurized sample infusion electrospray ionization mass spectrometry (PSI-ESI-MS) and FTIR spectroscopy was used to investigate the mechanism of a like-Barbier cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction (MCR). The use of charge-tagged aryl halides allowed for the detection of cobalt(II)-promoted hydrodehalogenation products. Although these products were also detected in the off-line ESI-MS monitoring, the ability of PSI-ESI-MS to track real-time changes in the reaction mixture composition proved cobalt(II) was responsible for the undesired transformation. The occurrence of cobalt(II)-promoted hydrodehalogenation as a side reaction in this MCR had not been considered in previous mechanistic proposals and represents an important mechanistic consideration.

Funding

FAPESP #2016/03036-4

History

Email Address of Submitting Author

mcindoe@uvic.ca

Institution

University of Victoria

Country

Canada

ORCID For Submitting Author

0000-0001-7073-5246

Declaration of Conflict of Interest

No conflict of interest

Version Notes

As submitted

Exports