Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions

Arenediazonium o-benzenedisulfonimides can be used as new and efficient reagents for Heck-type arylation reactions of some common substrates containing C-C multiple bonds, namely ethyl acrylate, acrylic acid, acroleyne, styrene and cyclopentene. The reactions were carried out in an organic solvent, in the presence of Pd(OAc)₂ as pre-catalyst, and gave rise to arylated products, for example, ethyl cinnamates, cinnamic acids, cinnamic aldehydes and stilbenes, possessing an (E)-configuration, and 1-arylcyclopentenes, in good to excellent yields. It is noteworthy that all the reactions led to the recovery, in greater than 80% yield, of o-benzenedisulfonimide, recyclable for the preparation of other diazonium salts.