Unprecedented substoichiometric use of hazardous aryl diazonium salts in the Heck-Matsuda reaction via a double catalytic cycle.

The first Heck-Matsuda reaction using a catalytic amount of diazonium salts has been discovered. The reaction proceeds through an unprecedented double catalytic cycle in which the electrophile is in situ generated through the reaction advancement. This concept features mild and safe conditions as hazardous aryl diazonium salts are not isolated anymore. Importantly, this sustainable procedure generates only environmentally friendly byproduct such as t-BuOH, H(2)O, and N(2).