Bis-Functionalization of 1,3-Dienes through 1,4-Conjugate Addition of Amphiphilic Bis-π-Allyl and Related Palladium Intermediates

Palladium-catalyzed three-component coupling of allylstannane, allyl chloride and a functionalized diene is described. Regioselective 1,4-functionalization of the Michael acceptor 1,3-diene is accomplished by the amphiphilic bis-π-allylpalladium complex. To the best of our knowledge, this is the first time a functionalized 1,3-butadiene has been used as a Michael acceptor. The scope of the present strategy is further extended to 1,4-allylation–oxyallylation of functionalized dienes.