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N ‐Arylation of Benzimidazole with Arylboronate, Boroxine and Boronic Acids. Acceleration with an Optimal Amount of Water
Author(s) -
Nishiura Katsutoshi,
Urawa Yoshio,
Soda Shigeru
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404193
Subject(s) - chemistry , benzimidazole , phenylboronic acid , boronic acid , yield (engineering) , coupling (piping) , coupling reaction , suzuki reaction , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , palladium , mechanical engineering , materials science , engineering , metallurgy
The coupling of benzimidazole 1 with arylboronate, boroxine, and boronic acids is accelerated efficiently by the addition of an optimal amount of water. This coupling reaction proceeds in nearly quantitative yield at 30 °C under an atmosphere of air within 24 hours. Under these conditions, the reaction tolerates both electron‐donating and electron‐withdrawing substituents at the ortho ‐, meta , or para ‐positions of the phenylboronic acid.