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Selective para ‐Cyanation of Alkoxy‐ and Benzyloxy‐Substituted Benzenes with Potassium Ferricyanide Promoted by Copper(II) Nitrate and Iodine
Author(s) -
Ren Yunlai,
Yan Mengjie,
Zhao Shuang,
Wang Jianji,
Ma Junying,
Tian Xinzhe,
Yin Weiping
Publication year - 2012
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.201200235
Subject(s) - chemistry , potassium ferricyanide , cyanation , alkoxy group , acetonitrile , iodine , ferricyanide , reagent , nitrile , medicinal chemistry , inorganic chemistry , potassium , solvent , organic chemistry , nuclear chemistry , alkyl , catalysis
Abstract A simple method was developed for selective para ‐cyanation of alkoxy‐ and benzyloxy‐substituted benzenes with 0.5 equivalents of potassium ferricyanide, 0.8 equivalants of copper(II) nitrate and 0.5 equivalents of iodine in acetonitrile. Among various phenyl carbon‐hydrogen bonds, those at the para ‐position with regard to the alkoxy or benzyloxy groups were selectively cyanated in 20% to 87% yields (23 examples). The present method uses commercially available reagents, and can be performed on a ten gram‐scale. Interestingly, methoxybenzene was cyanated in 32% yield in the absence of potassium ferricyanide, which suggests that the nitrile group of a part of the product is possibly from the solvent acetonitrile.