Synthesis of novel amphiphilic pyridinylboronic acids

Abstract

Novel 3-alkoxy-2-pyridinylboronic acids bearing, in their 3-position, linear alkoxy or perfluoroalkoxy chains with n carbon atoms (n = 6, 8, 10, 12 and 18) 2a-2g are synthesized from 2-bromo-3-pyridinol, which is the common starting product. Our alternative procedure for the synthesis of 3-alkoxy-2-bromopyridine in a phase-transfer catalysis system is to carry out the reaction in a solid-liquid medium in the presence of a quaternary ammonium salt under microwave irradiation. General and versatile synthetic methods have been developed for preparation of a large variety of new 2-pyridinylboronic acids bearing two alkylated or perfluoroalkylated side chains with an ether junction in the 3-position. Copyright © 2003 John Wiley & Sons, Ltd.