The synthesis of furanones via rhodium-catalyzed carbonylative addition reactions of arylboronic acids to alkynes

Abstract

This study reveals that 5-Aryl-2(5H)-furanones can be synthesized by rhodiumcatalyzed reaction of arylboronic acids with internal alkynes under a CO atmosphere.In this thesis, relatively mild and simple method for synthesis of 2(5H)-furanones was developed. Our method was found to be applicable for various arylboronic acids and alkynes.The methodology of this study is well applicable for ortho-, para- and metasubstituted phenylboronic acids. But slightly higher yields were obtained with parasubstituted phenylboronic acids than ortho- or meta- substituted ones.It was found that when an asymmetric alkyne is used under the optimized conditions, aroylation occurs more on the electron deficient acetylenic carbon as compared with electron rich acetylene when aroylrhodium(I) species undergoes 1,2-addition to the carbon-carbon triple bond in the reaction. That affects the ratio of isomeric yields of furanones which were produced in the reactions of asymmetric alkynes with phenylboronic acid.2(5H)-Furanones that we synthesized can be used in many areas such as food manufacturing, perfume and medicinal industries.