Heck Cross-Coupling of Aryldiazonium Tetrafluoroborate with Acrylates Catalyzed by Palladium on Charcoal

A property-activity relationship study of various palladium supported on charcoal (Pd/C) catalysts has been undertaken for the Heck reaction of aryldiazonium tetrafluoroborate with acrylates. The optimized protocol enables the cross-coupling with a low loading of palladium at room temperature in technical grade methanol. Although the catalyst could not be recycled at this time, measurement of the palladium content by inductively coupled plasma mass spectrometry (ICP-MS) shows low palladium contamination of the solvent and product, rendering this method safer for the environment compared to homogeneous conditions.