Heck–Matsuda reaction

[4][2][3] Allylic alcohols, conjugated alkenes, unsaturated heterocycles and unactivated alkenes are capable of being arylated with arenediazonium salts using simple catalysts such as palladium acetate (Pd(OAc)2) or tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) at room temperature in air, and in benign and conventional solvents.

[1] In addition to the intermolecular variant of the HM reaction, intramolecular cyclization processes have also been developed for the construction of a range of oxygen and nitrogen heterocycles.

[1] The catalytic cycle for the Heck-Matsuda arylation reaction has four main steps: oxidative addition, migratory insertion or carbopalladation, syn β-elimination and reductive elimination.

The proposed Heck catalytic cycle involving cationic palladium with diazonium salts was reinforced by studies with mass spectrometry (ESI) by Correia and co-workers.

[1] These results also show the complex interactions that occur in the coordination sphere of palladium during the Heck reaction with arenediazonium salt.