Facile synthesis of aryl-substituted pyridines via Suzuki-Miyaura approach

KARADENİZ E., ZORA M., KILIÇASLAN N. Z.

TETRAHEDRON, cilt.71, sa.47, ss.8943-8952, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 71 Sayı: 47
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.tet.2015.09.063
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8943-8952
  • Anahtar Kelimeler: Pyridine, Arylpyridine, Iodopyridine, Coupling, Suzuki-Miyaura reaction, Ferrocene, PROPARGYLIC BETA-ENAMINONES, ONE-POT SYNTHESIS, DIELS-ALDER REACTIONS, TOPOISOMERASE-I INHIBITION, DE-NOVO SYNTHESIS, REGIOSELECTIVE SYNTHESIS, INTRAMOLECULAR CYCLIZATION, POLYSUBSTITUTED PYRIDINES, OXIDATIVE AROMATIZATION, HETEROCYCLIC AZADIENES
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

A facile and efficient synthetic route to arylpyridines is reported. When heated with boronic acids in the presence of 5 mol % PdCl2(PPh3)(2) and KHCO3 in 4:1 DMF/H2O solution at 110 degrees C, 5-iodopyridines have undergone Suzuki-Miyaura coupling reactions to afford 5-aryl-substituted pyridines in good to excellent yields. The coupling reaction has been found to be general for a broad range of iodopyridines and boronic acids, and demonstrated good tolerance to a variety of aliphatic, aromatic, heteroaromatic and ferrocenyl groups with electron-withdrawing and electron-donating substituents. This coupling approach could accommodate various functional groups and provide rapid access to a library of functionalized arylpyridines of pharmacological interest. The starting 5-iodopyridines have been prepared from alpha,beta-alkynic ketones, involving conjugate addition of propargylamine to alkynones, followed by metal-catalyzed cross-coupling of the resulting N-propargylic beta-enaminones with aryl iodides and electrophilic cyclization with molecular iodine. (C) 2015 Elsevier Ltd. All rights reserved.