Diels-Alder reactions of cyclopentadienones with aryl alkynes to form biaryl compounds

ORGN 587

Anthony J. Pearson, ajp4@case.edu and Yan Zhou, yxz48@case.edu. Department of Chemistry, Case Western Reserve University, 433 Millis, 2074 Adelbert Rd, Cleveland, OH 44106
Cyclopentadienones have a high potential for organic synthesis. Among reactions of cyclopentadienones, Diels-Alder reactions are the most extensively studied. Cyclopentadienones can react as dienes in Diels-Alder reactions with dienophiles. Previous work in our laboratory has shown that monocyclic cyclopentadienones, which are obtained from silicon tethered Fe(CO)5-promoted cyclocarbonylation of alkynes, are good candidates for preparing aromatic and biaryl structures via Diels-Alder type reactions and subsequent thermal decarbonylation. In this study, we aim to evaluate and expand Diels-Alder applications on cyclopentadienones. Th biaryl structures formed by this methodology could find use as intermediates in the synthesis of complex molecules.