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Application of palladacycle catalyst in the synthesis of mono‐arylpyridyl bromides
Author(s) -
Zhang Jinli,
Wu Yangjie,
Zhu ZhiWu,
Ren Gerui,
Mak Thomas C. W.,
Song Maoping
Publication year - 2007
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1294
Subject(s) - chemistry , catalysis , toluene , methanol , organic chemistry , medicinal chemistry , combinatorial chemistry
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 palladacycle (catalyst II ) catalyzed Suzuki reaction of 3,5‐dibromopyridine with a series of arylboronic acids—ester under the conditions of K 2 CO 3 –toluene–methanol (4:1, v/v), reflux (75 °C), 5.6 equiv. of 3,5‐dibromopyridine with the ratio (mono:bis) ranging from of 99:1 to 90:10. This new method could also be used to easily achieve pyridylpyridyl bond formation to afford 3‐bromo‐5‐pyridylpyridine ( 3j ). Copyright © 2007 John Wiley & Sons, Ltd.