First examples of a tosylate in the palladium-catalyzed Heck cross coupling reaction

The palladium-catalyzed cross coupling Heck reaction of tosylate (2) and methyl acrylate has been developed as an efficient method for carboncarbon bond formation. The tosylate (2) was reacted with methyl acrylate using palladium acetate as catalyst to provide 3-(3-oxo-1-cyclohexen-1-yl)-2-propenoic acid methyl ester (3) in excellent yield. The coupling reaction of tosylate (9) under the similar conditions also provided the dienoic acid methyl ester (10) in >80% overall yield. The effect of reaction parameters such as temperature and catalyst as well as the ratio of palladium acetate to triphenylphosphine on the reaction rate has been studied.