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Synthesis and characterization of N-heterocyclic carbene palladium complex and its application on direct arylation of benzoxazoles and benzothiazoles with aryl bromides
(Taylor & Francis Ltd, 2009) Arslan, Hakan; Ozdemir, Ismail; Vanderveer, Don; Demir, Serpl; Cetinkaya, Bekir
A mixed-halogen bis(1-(4-tert-butylbenzyl)-3-(2, 4, 6-trimethylbenzyl)-1H-benzo[d]imidazol-2-ylidene) palladium(II) complex, trans-[Pd(Cl0.7Br0.3)2(C28H32N2)2], has been synthesized and characterized by elemental analysis, 1H-NMR, 13C-NMR, and IR spectroscopy, and single crystal X-ray diffraction. The palladium in the mononuclear complex is four-coordinate in a square-planar configuration with two carbenes of two benzo[d]imidazole rings and two halides. The two halides are disordered between Br and Cl, with the Cl: Br ratio approximately 0.7 : 0.3. The angles C1-Pd1-Br1, 88.63(11)degrees and C1i-Pd1-Br1i, 91.37(11)degrees (i: 1-x, 1-y, 1-z) in the coordination sphere are very close to the ideal value of 90 degrees. The Pd-X distance is slightly longer than other carbene derivative Pd-Cl single bond distances and slightly shorter than Pd-Br single bond distances. These results agree with the Cl/Br disorder at the halogen position. The palladium-carbene complex was tested as a catalyst in the direct arylation reaction of benzoxazoles and benzothiazoles with aryl bromides.