Bis-functionalization of 1,3-dienes through 1,4-conjugate addition of amphiphilic bis-pi-allyl and related palladium intermediates

Abstract

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--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.