Synthesis of novel amphiphilic pyridinylboronic acids

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.