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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| Published in | Organometallics Vol. 22; no. 20; pp. 4158 - 4162 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
29.09.2003
Amer Chemical Soc |
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| Abstract | 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). |
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| AbstractList | 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). 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). |
| Author | Drake, Michael D Detty, Michael R Bateman, Margaret A |
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| Cites_doi | 10.1021/om020511p 10.1039/b008198l 10.1021/ja002649+ 10.1021/jo0057710 10.1039/b206859c 10.1021/ja028030k 10.1021/cr00021a014 10.1016/0040-4039(94)85333-9 10.1021/ja01243a504 10.1021/om960476k 10.1021/jo00431a056 10.1021/ol9902935 10.1021/ja01523a035 10.1021/ja01323a010 10.1021/cr00002a004 10.1039/9781847550132 10.1139/v83-183 10.1021/ja00816a048 10.1080/00397918608078772 10.1016/S0022-328X(99)00343-5 10.1016/S0040-4039(98)01305-7 |
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| Keywords | KETONES CONVERSION SELECTIVE BROMINATION OXIDATIONS OLEFINS HALOGENATION BENZENE-SELENINIC ACID H2O2 EPOXIDATION |
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| Snippet | 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.... |
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| SubjectTerms | Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Physical Sciences Science & Technology |
| Title | Substituent Effects in Arylseleninic Acid-Catalyzed Bromination of Organic Substrates with Sodium Bromide and Hydrogen Peroxide |
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