Functionalization of beta-C-H bonds of thiophenes such as their vinylation is more challenging than for their alpha-positions. The use of Pd-catalysis allowed us to vinylate such thienyl beta-positions. Oxidative addition of 2-(2-bromoaryl)thiophenes to palladium followed by a Pd 1,4-migration activates these thienyl beta-C-H positions, then, classical Pd-catalyzed Heck reaction gives the beta-vinylated 2-arylthiophene derivatives. In the course of this coupling reaction, the bromide substituent on the aryl unit acts as a traceless directing group. It should also be mentioned that the created C-C bond results from the functionalization of two C-H bonds. This synthesis scheme tolerates a range of substituents on both the aryl ring and the alkene. In addition, this procedure employs an easily available air-stable catalyst and an inexpensive base. This reaction allows the programmed Pd-catalyzed synthesis of 2,3,5-trisubstituted thiophenes using first Suzuki C2-coupling, then Pd-catalyzed direct C5-arylation and finally Pd 1,4-migration Heck C3-vinylation.