Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 13, Pages 6094-6104Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5008064
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Funding
- Ministy of Education, Culture, Sports, Science and Technology of Japan [24750033]
- Iodine Research Project of Chiba University
- Grants-in-Aid for Scientific Research [24750033] Funding Source: KAKEN
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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 Bronsted 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.
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