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Cu(II) bromide catalyzed oxidation of aldehydes and alcohols
Author(s) -
Das Rima,
Chakraborty Debashis
Publication year - 2011
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.1783
Subject(s) - chemistry , chemoselectivity , catalysis , conjugated system , yield (engineering) , alcohol oxidation , bromide , alcohol , organic chemistry , carboxylic acid , aldehyde , polymer , materials science , metallurgy
A variety of aromatic, aliphatic and conjugated aldehydes and alcohols were transformed to the corresponding carboxylic acids and ketones with a quantitative conversion in high yields with 70% t ‐BuOOH solution in water in the presence of catalytic (5 mol%) amounts of CuBr 2 under room temperature conditions. The conversion of 4‐methoxybenzaldehyde to 4‐methoxybenzoic acid is extremely facile in MeCN at ambient temperature in the presence of 5 mol% CuBr 2 and 2 equiv. 70% t ‐BuOOH (water) as the oxidant. Oxidation with t ‐BuOOH (water) alone in MeCN was found to be negligible. The scope of our catalytic system is applicable for a wide range of aromatic, conjugated and aliphatic substrates. These aldehydes were converted to the corresponding carboxylic acids in good isolated yields in reasonable times. It is pertinent to mention here that mild halogenic oxidants like hypochlorites, chlorites and NBS are not suitable for substrates with electron‐rich aromatic rings, olefinic bonds and secondary hydroxyl groups. Substitutions at different positions on the phenyl ring do not hinder the reaction, although the reaction time is affected. Oxidation of α,β unsaturated derivatives resulted in the formation of the expected acid in good yield. In addition, the transformation of secondary alcohols to ketones is extremely facile. No recemization was observed for menthone. This method possesses a wide range of capabilities since it can be used with other functional groups which may not tolerate oxidative conditions, involves fairly simple method for work‐up, exhibits chemoselectivity and proceeds under ambient conditions. The resulting products are obtained in good yields within reasonable time. Copyright © 2011 John Wiley & Sons, Ltd.