Biphenyl 3-and 4-mono and 4, 4 '-dicarbaldehyde as Electrophiles and Unusual Michael Acceptors in the Baylis-Hillman Reaction: Synthesis of Functionalized Biphenyl Derivatives

The Morita-Baylis-Hillman (MBH) reaction of biphenyl 3- and 4- mono aldehydes and 4, 4 '-dicarbaldehyde as electrophiles and a number of unexplored activated alkenes afforded highly functionalized biphenyl derivatives in excellent yield. Synthetic transformations of mono and bis MBH adducts thus obtained have been demonstrated by isomerization of MBH adducts with different nucleophiles, Friedel-Crafts arylation reaction of bromo isomerized biphenyl adducts, Eglinton coupling of biphenyl propargyl MBH adduct derivative and [3+2]- azomethine ylide cycloaddition of methyl acrylate derived biphenyl aldehydes afforded highly functionalized arylated and heterocyclic derivatives in very good yield.