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


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

TETRAHEDRON, vol.71, no.47, pp.8943-8952, 2015 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 71 Issue: 47
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tet.2015.09.063
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.8943-8952

Abstract

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.