Pd-N-heterocyclic carbene complex catalysed C-H bond activation of 2-isobutylthiazole at the C5 position with aryl bromides

Khan S., Bugday N., YAŞAR S., Ullah N., ÖZDEMİR İ.

NEW JOURNAL OF CHEMISTRY, cilt.45, sa.14, ss.6281-6292, 2021 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 45 Sayı: 14
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1039/d1nj00514f
  • Dergi Adı: NEW JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Biotechnology Research Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, DIALNET
  • Sayfa Sayıları: ss.6281-6292
  • İnönü Üniversitesi Adresli: Evet

Özet

An effective and efficient catalytic system has been reported for the synthesis of C5-arylated 2-isobutylthiazoles. Pd-N-heterocyclic carbene complexes like [Pd(mu-Cl)Cl(SIPr)](2) (2) and (LCl2Pd-SIPr) (3: L = PPh3, 4: L = Py; 5: L = 3-CHO-Py) were synthesized and characterized by H-1, C-13, P-31 NMR, LC-MS/MS, elemental analysis, and FTIR spectroscopy. These Pd-N-heterocyclic carbene complexes were assessed for the first time as catalysts for the C-H arylation reaction of 2-isobutylthiazole at the C5 position with different (hetero)aryl bromides. The catalytic system showed a low catalyst loading (1 mol%) and did not require the use of additional additives such as pivalic acid. The catalytic system developed with these catalysts enables the synthesis of fine chemicals in high yields under aerobic or anaerobic conditions. All complexes showed moderate to good yields in the C5 direct arylation of 2-isobutylthiazole, while complex 2 exhibited higher catalytic activity than the other complexes.