Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol- 5-ylidene)palladium(II) dichloride and diacetate. Suzuki-Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

Abstract

trans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple Suzuki-Miyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and with high turnover numbers. With 1,4-dibromobenzene the catalyst was found to be active for up to 13 consecutive cycles with a turnover number of 1260. The polyarylarenes were obtained in pure form after crystallization once without recourse to chromatographic purification. The single-crystal X-ray structures of the chloro (1) as well as the corresponding acetato (2) complexes are also reported and compared with the corresponding complexes of 1,4-diphenyl-3-methyl- 1,2,3-triazol-5-ylidene as the ligand. © 2013 Shaik et al.