Direct C-H Bond Arylation of C2-Blocked Pyrrole with Aryl Halides Using Palladium(II)-N-Heterocyclic Carbene Catalysts

KALOĞLU M., KALOGLU N., ÖZDEMİR İ.

CHEMISTRYSELECT, cilt.3, sa.20, ss.5600-5607, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 3 Sayı: 20
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1002/slct.201801045
  • Dergi Adı: CHEMISTRYSELECT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5600-5607
  • Anahtar Kelimeler: Benzimidazolium salt, Direct C-H bond arylation, N-Heterocyclic carbene, Palladium, Pyrrole, ROOM-TEMPERATURE, DERIVATIVES, HETEROAROMATICS, FUNCTIONALIZATION, COMPLEXES, THIAZOLES, ACCESS, SYSTEM, FURANS, C-2
  • İnönü Üniversitesi Adresli: Evet

Özet

Herein we report synthesis of seven new palladium(II)-NHC complexes with the general formula [PdX2(NHC)(2)], (NHC=1,3-dialkylbenzimidazol-2-ylidene, X = Cl or Br). The structures of all the new compounds were characterized by (HNMR)-H-1, (CNMR)-C-13, FT-IR spectroscopy and elemental analysis techniques. The catalytic activities of palladium(II)-NHC complexes were tested in the direct C-H bond arylation of C2-blocked pyrrole with various aryl halides in presence of 1mol% catalyst loading at 120 degrees C for 1-16 h. Under the given conditions, palladium(II)-NHC complexes showed the good catalytic performance for the direct C-H bond arylation of C2-blocked pyrrole with aryl bromides, and with readily available and inexpensive aryl chlorides. In all cases, the C-H bond arylation regioselectively produced C5-arylated products in moderate to high yields.