Palladium catalyzed three component coupling reaction between chromones, alcohols, and allylic acetates: diversity-oriented synthesis of highly substituted chromones

Abstract

This paper describes the palladium catalyzed highly efficient three component coupling (TCC) reactions between chromones, allylic acetates, and alcohols, which lead to a library of multiply substituted chromones. The activity of various palladium catalysts, such as Pd(PPh 3) 4 and Pd 2dba 3·CHCl 3 and their combination with various bisphosphine ligands, was investigated by using THF as a solvent, which revealed that Pd(PPh 3) 4 catalyst was the best one. The reaction most probably proceeds via the formation of benzopyrilium cation, generated from the reaction between chromones and allyl acetate, in the presence of palladium catalyst. The subsequent trapping of the benzopyrilium cation by alcohols would give the corresponding products in excellent yields. This alkoxy-allylation reaction was highly diastereoselective and only one diastereomer was obtained in all the cases.