3-(2-Propenyl)benzothiazolium bromide (A) provides a direct and simple entry to Pd(II) complexes with N,S-heterocyclic carbene (NSHC) ligands functionalized with an allyl pendant with hemilabile potential. Addition of salt A to Pd(OAc)₂ eliminates HOAc and affords the bis(carbene) complexes cis-[PdBr₂(NHSC)₂] (cis-1, NSHC = 3-(2-propenyl)benzothiazolin-2-ylidene) and trans-[PdBr₂(NHSC)₂] (trans-1) along with the monocarbene complexes [PdBr₂(NSHC)] (2) and trans-[PdBr₂(benzothiazole-κN)(NSHC)] (3) as minor side products. Salt-metathesis of cis-1 with AgO₂CCF₃ yields the mixed dicarboxylato-bis(carbene) complex cis-[Pd(O₂CCF₃)₂(NSHC)₂] (4). Complexes cis-1, trans-1 and 4 were characterized by multinuclear NMR spectroscopies, ESI mass spectrometry and elemental analysis. The molecular structures of complexes cis-1, 2 and 3 have been determined by X-ray single crystal diffraction. Complexes cis-1 and 4 as well as an in situ mixture of Pd(OAc)₂ and salt A are active toward Suzuki–Miyaura coupling of aryl bromides and activated aryl chlorides giving good conversions.