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

The cross-coupling of N-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.

Automated summary

The cross-coupling of N-tosylhydrazones and aryl halides to form carbon-carbon bonds, producing 1,1-disubstituted alkenes, has been widely used in chemistry, but its mechanism remains experimentally unexplored. The combination of benchtop NMR and real-time mass spectrometry allows for monitoring of catalytic intermediates and the rate of product formation.