1-Chloro-1-cyclopentene undergoes cross-coupling reaction with arylboronic acids, arylzinc reagents and thiols catalyzed by air-stable palladium complexes to yield the corresponding styrene derivatives, biaryls, and thioethers. Palladium-catalyzed aminocarbonylations of 1-chloro-1-cyclopentene and benzyl amine has been studied.