Substituent Effects in Arylseleninic Acid-Catalyzed Bromination of Organic Substrates with Sodium Bromide and Hydrogen Peroxide

Arylseleninic acids were found to be catalysts for the oxidation of bromide with hydrogen peroxide in a two-phase mixture of ether and pH 6 phosphate buffer. Benzeneseleninic acid (3) and 4-methoxyphenylseleninic acid (4) were more efficient catalysts than 3,5-bis(trifluoromethyl)phenylseleninic aci...

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Bibliographic Details
Published inOrganometallics Vol. 22; no. 20; pp. 4158 - 4162
Main Authors Drake, Michael D, Bateman, Margaret A, Detty, Michael R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.09.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
CONVERSION
SELECTIVE BROMINATION
OXIDATIONS
OLEFINS
HALOGENATION
BENZENE-SELENINIC ACID
H2O2
EPOXIDATION
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Summary:Arylseleninic acids were found to be catalysts for the oxidation of bromide with hydrogen peroxide in a two-phase mixture of ether and pH 6 phosphate buffer. Benzeneseleninic acid (3) and 4-methoxyphenylseleninic acid (4) were more efficient catalysts than 3,5-bis(trifluoromethyl)phenylseleninic acid (1), 4-nitrophenylseleninic acid (2), 4-dimethylaminophenylseleninic acid (5), and 2,4,6-trimethylphenylseleninic acid (6). A variety of organic substrates were efficiently brominated under these conditions using 5−10 mol % of commercially available benzeneseleninic acid (3).
Bibliography:istex:BAB918200CE975E3169D6DEB3EDC3C24F2E2221F
ark:/67375/TPS-N98Z7WZ2-R
ISSN:0276-7333
1520-6041
DOI:10.1021/om0340239