Regioselective synthesis of naphthalenes from modified Baylis–Hillman adducts via a Pd-catalyzed cyclization: 5- exo-carbopalladation, C(sp 3)–H activation to cyclopropane, ring-opening, and aromatization cascade

Abstract

Modified Baylis–Hillman adducts having 2-bromophenyl acetonitrile moiety at the primary position underwent a Pd-catalyzed cascade reaction to provide poly-substituted naphthalene derivatives in reasonable yields. The reaction involved a sequential 5- exo-carbopalladation, C(sp 3)–H activation to cyclopropane, ring-opening and concomitant aromatization processes.