Revisiting the mechanism of the Fujiwara-Moritani reaction

Abstract

The Fujiwara-Moritani reaction between p-methylacetanilide and n-butyl acrylate, catalysed by Pd(OAc)2 in the presence of toluenesulfonic acid and benzoquinone, was (re-)investigated using reaction calorimetry and complementary spectroscopic methods. The (most) active catalyst was identified and the catalytic turnover rate was found to be independent of all stoichiometric reagents. Catalyst regeneration and deactivation pathways are discussed.