Conjugated enynes have been not only found in the electro- and optical materials natural compounds, and pharmaceuticals but also employed as useful synthetic building blocks due to the fact that they can be diversely transformed into the important moieties. Among them, conjugated enynones have been attracted attention in the synthesis of bioactive agents and used as starting materials for the preparation of useful organic molecules such as allene, cyclooctatetraene, pyrrolizine, chromene, fused ring and polycyclic compounds. Among synthetic methods for enyone, Sonogashira type coupling reactions of 3-oxoalkenyl halides (or pseudo halide) and terminal alkyne has been widely used as a straightforward tool. However, the reaction with 3-oxoalkenyl tosylate was very rare even though alkenyl tosylate was easily accessible and stable. Moreover, the coupling reaction with alkynyl carboxylic acid has never been reported so far. Herein we report the decarboxylative coupling reaction of alkynyl carboxylic acid and 3-oxoalkenyl tosylates. A variety of alkynyl carboxylic acids were coupled with 3-oxocyclohexenyl tosylates to provide the corresponding enynones in good to excellent yields. Alkenyl tosylate is readily prepared, stable and cost efficient. This catalytic system is phosphine free and showed good tolerance toward functional groups such as chloride, cyano, nitro, ester, aldehyde and alcohol. In addition, it was found that phenylpropiolic acid showed higher reactivity in the reaction with alkenyl toslyate than phenyl acetylene.