Pd(II) complexes of N,S-heterocyclic carbenes with pendant and coordinated allyl function and their Suzuki coupling activities

3-(2-Propenyl)benzothiazolium bromide () 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 to Pd(OAc)(2) eliminates HOAc and affords the bis(carbene) complexes cis-[PdBr(2)(NHSC)(2)] (cis-, NSHC = 3-(2-propenyl)benzothiazolin-2-ylidene) and trans-[PdBr(2)(NHSC)(2)] (trans-) along with the monocarbene complexes [PdBr(2)(NSHC)] () and trans-[PdBr(2)(benzothiazole-kappaN)(NSHC)] () as minor side products. Salt-metathesis of cis- with AgO(2)CCF(3) yields the mixed dicarboxylato-bis(carbene) complex cis-[Pd(O(2)CCF(3))(2)(NSHC)(2)] (). Complexes cis-, trans- and were characterized by multinuclear NMR spectroscopies, ESI mass spectrometry and elemental analysis. The molecular structures of complexes cis-, and have been determined by X-ray single crystal diffraction. Complexes cis- and as well as an in situ mixture of Pd(OAc)(2) and salt are active toward Suzuki-Miyaura coupling of aryl bromides and activated aryl chlorides giving good conversions.