Heck coupling in the gas phase: Examination of the reaction mechanism by ion/molecule reactions and mass spectrometry

The Heck reaction of isoprene with (p-iodophenyl)-trimethylammonium iodide was conducted in the gas phase. Relevant species of the catalytic cycle including the ionic product of the Pd-catalyzed coupling reaction were reliably characterized by exact ion mass measurements and by characteristic product ions generated by tandem-MS.

Figure optionsDownload high-quality image ( K)Download as PowerPoint slideHighlights
► Labile Heck coupling reaction intermediates and the coupling product are investigated in the gas phase.
► Charge-tagging, ESI-MSn, ion/molecule reactions and exact ion mass measurements are performed.
► A LTQ-Orbitrap Instrument is modified for the study.
► The results suggest that the Heck reaction proceeds via the accepted mechanism in solution and in the gas phase.