Application of palladacycle catalyst in the synthesis of mono-arylpyridyl bromides

作者:Zhang Jinli; Wu Yangjie*; Zhu Zhiwu; Ren Gerui; Mak Thomas C W; Song Maoping
来源:Applied Organometallic Chemistry, 2007, 21(11): 935-940.
DOI:10.1002/aoc.1294

摘要

The mono-arylpyridyl bromides are very useful key intermediates that can be further functionalized. to generate bioactive compounds. It is possible to obtain mono-arylation products of 3,5-dibromopyridine with high preferentiality and high yields by air- and moisture-stable pallaclacycle (catalyst II) catalyzed Suzuki reaction of 3,5-dibromopyridine with a series of arylboronic acids-ester under the conditions of K2CO3-toluene-methanol (4:1, v/v), reflux (75 degrees C), 5.6 equiv. of 3,5dibromopyridine with the ratio (mono: bis) ranging from of 99: 1 to 90: 10. This new method could also be used to easily achieve pyridyl-pyridyl bond formation to afford 3-bromo-5-pyridylpyridine (3j).