A mechanistic investigation of the Pd-catalyzed cross-coupling between <i>N</i> -tosylhydrazones and aryl halides

Abstract

The cross-coupling of <i>N</i>-tosylhydrazones and aryl halides forms carbon-carbon bonds, producing 1,1-disubstituted alkenes. Though it has proven extremely useful in several fields of chemistry, its mechanism remains experimentally unexplored. Combining benchtop NMR and real-time mass spectrometry afforded the ability to monitor the catalytic intermediates as well as the rate of product formation.