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

Abstract

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.