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Selective Oxidation of Alcohols with Alkali Metal Bromides as Bromide Catalysts: Experimental Study of the Reaction Mechanism

Author:
Moriyama, Katsuhiko, Takemura, Misato, Togo, Hideo
Source:
Journal of organic chemistry 2014 v.79 no.13 pp. 6094-6104
ISSN:
1520-6904
Subject:
alcohols, aldehydes, carbonyl compounds, carboxylic acids, catalysts, chemical structure, hydrogen peroxide, organic chemistry, oxidants, oxidation, potassium bromide, reaction mechanisms
Abstract:
A bromide-catalyzed oxidation of alcohols was developed which proceeded in the presence of an alkali metal bromide and an oxidant under mild conditions. The reaction involved an organic-molecule-free oxidation using KBr and Oxone and a Brønsted acid assisted oxidation using KBr and aqueous H₂O₂ solution to provide a broad range of carbonyl compounds in high yields. Moreover, the bromide-catalyzed oxidation of primary alcohols enabled the divergent synthesis of carboxylic acids and aldehydes under both reaction conditions in the presence of TEMPO. A possible catalytic mechanism was suggested on the basis of various mechanistic studies.
Agid:
5502420