Diazonium salts aryl, coupling with alkenes

Aryl diazonium salts can be used coupled with alkenes in a Heck-Uke reaction (12-15)7 Other reactive aryl species also couple with aryldiazonium salts in the presence of a palladium catalyst7 A Suzuki type coupling (13-9) has also been reported using arylboronic acids, aryldiazonium salts and a palladium catalyst/ ... 

The Pd )-catalyzed reaction of aryl diazonium salts with mono-substituted alkenes [1] was found to be an interesting alternative to the well-known Pd - catalyzed arylhalide alkene coupling (Heck type reaction) or the copper mediated reaction of aryl diazonium salts with alkenes (Meerwein arylation) [2], The reaction can be run without isolation of the diazonium salt in presence of only 0.5 to 1 mol% of the Palladium catalyst in a one pot procedure, in high yield and under nuld conditions. The resulting styrene is reduced in a subsequent hydrogenation step with an in situ generated heterogeneous Pd-catalyst. The combination of three reaction steps without isolation of intermediates and the virtually complete recovery of the Pd-metal at the end of the reaction sequence makes this process [4] extremely efficient. 

Besides the traditional coupling between alkenes and aryl (vinyl) halides, other functionalized aryl derivatives can also couple with alkenes in the Heck reaction, including aryl silanes,stannanes, bismuth, antimony,triflates, boric acid, phosphonic acid, carboxylic acid, and diazonium salt. ... 

---