ortho-Disubstitution reactions of aromatic rings with homo-conjugated bicyclo[2.2.2]octa-2,5-diene derivatives in the presence of palladium(II) acetate

Bicyclo[2.2.2]octa-2,5-diene derivatives and reacted with aromatic compounds such as benzene, naphthalene, anthracene, phenanthrene, and tropone in the presence of Pd(OAc)2 to afford ortho-disubstituted aromatics and . Since the yields and regioselectivity were generally low, the reaction conditions were optimized by using iodoarenes as reagents to provide sufficient yields and regioselectivity. In order to investigate reactivities of diene moieties, several kinds of homo-conjugated dienes were surveyed for the reaction. Only dienes containing a bicyclo[2.2.2]octa-2,5-diene skeleton gave the ortho-disubstituted aromatics.