Synthesis and characterization of N-heterocyclic carbene palladium complex and its application on direct arylation of benzoxazoles and benzothiazoles with aryl bromides

ARSLAN H., ÖZDEMİR İ., Vanderveer D., Demir S., Cetinkaya B.

JOURNAL OF COORDINATION CHEMISTRY, cilt.62, sa.16, ss.2591-2599, 2009 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 62 Sayı: 16
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1080/00958970902923313
  • Dergi Adı: JOURNAL OF COORDINATION CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2591-2599
  • Anahtar Kelimeler: Synthesis, N-Heterocyclic carbene, Benzoxazoles, Direct arylation, Palladium complex, Single crystal structure, CROSS-COUPLING REACTIONS, CRYSTAL-STRUCTURE, CATALYZED ARYLATION, SUZUKI-MIYAURA, LIGANDS, HALIDES, PRECURSORS, REACTIVITY, CHEMISTRY, OXAZOLE
  • İnönü Üniversitesi Adresli: Evet

Özet

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.