Imidazole, pyrimidine and diazepine containing heteroaryl-substituted heterocyclic salts as efficient ligand precursors for Mizoroki-Heck coupling reaction: synthesis, structural characterization and catalytic activities

Gok Y., Akkoc S., AKKURT M., Tahir M. N.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, cilt.11, sa.6, ss.1767-1774, 2014 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 11 Sayı: 6
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1007/s13738-014-0449-z
  • Dergi Adı: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1767-1774
  • İnönü Üniversitesi Adresli: Evet

Özet

The nine new heteroaryl-substituted imidazolidinium (1a-c), pyrimidinium (2a-c) and diazepinium (3a-c) salts as N-heterocyclic carbene (NHC) precursors were synthesized in good yields and entirely characterized using elemental analyses and conventional spectroscopic methods. In situ formed complexes from heterocyclic salts (1-3), Pd(OAc)(2) and in the presence of KOBu (t) as a base were tested as catalysts for the Mizoroki-Heck coupling reaction in an aqueous media and very high yields were achieved. 1,3-Di(5-methylthiophen-2-ylmethyl)pyrimidinium hexafluorophosphate salt (2b) was structurally characterized by single-crystal X-ray diffraction. In the 2b compound (C16H21N2S2)(+)[PF6](-), the terminal thiophene rings are twisted with a dihedral angle of 72.8(3)A degrees. In the pyrimidine ring, the three successive C atoms between the N atoms are disordered over two positions [occupancy ratio 0.753(12):0.247(12)]. In the crystal, neighboring molecules are linked by C-HaEuro broken vertical bar F hydrogen bonds, running along the b axis.