Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes
The iodo-oxyimidation of styrenes with the N-hydroxyimide/I2/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34–91%. A plausible reaction pathway includes the...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.14.188 |
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doaj-7da32a40af2e4f9a924a8809f5aff2c02021-02-02T01:37:25ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-08-011412146215510.3762/bjoc.14.1881860-5397-14-188Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenesIgor B. Krylov0Stanislav A. Paveliev1Mikhail A. Syroeshkin2Alexander A. Korlyukov3Pavel V. Dorovatovskii4Yan V. Zubavichus5Gennady I. Nikishin6Alexander O. Terent’ev7N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian FederationNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str., 28, 119991 Moscow, Russian FederationNational Research Center “Kurchatov Institute”, Akademika Kurchatova pl., 1, 123182 Moscow, Russian FederationNational Research Center “Kurchatov Institute”, Akademika Kurchatova pl., 1, 123182 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian FederationThe iodo-oxyimidation of styrenes with the N-hydroxyimide/I2/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34–91%. A plausible reaction pathway includes the addition of an imide-N-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine. It was shown that the iodine atom in the prepared iodo-oxyimides can be substituted by various nucleophiles.https://doi.org/10.3762/bjoc.14.188free radicalshypervalent iodineimide-N-oxyl radicalsiodinationN-hydroxyimidesoxidative functionalization |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Igor B. Krylov Stanislav A. Paveliev Mikhail A. Syroeshkin Alexander A. Korlyukov Pavel V. Dorovatovskii Yan V. Zubavichus Gennady I. Nikishin Alexander O. Terent’ev |
| spellingShingle |
Igor B. Krylov Stanislav A. Paveliev Mikhail A. Syroeshkin Alexander A. Korlyukov Pavel V. Dorovatovskii Yan V. Zubavichus Gennady I. Nikishin Alexander O. Terent’ev Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes Beilstein Journal of Organic Chemistry free radicals hypervalent iodine imide-N-oxyl radicals iodination N-hydroxyimides oxidative functionalization |
| author_facet |
Igor B. Krylov Stanislav A. Paveliev Mikhail A. Syroeshkin Alexander A. Korlyukov Pavel V. Dorovatovskii Yan V. Zubavichus Gennady I. Nikishin Alexander O. Terent’ev |
| author_sort |
Igor B. Krylov |
| title |
Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes |
| title_short |
Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes |
| title_full |
Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes |
| title_fullStr |
Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes |
| title_full_unstemmed |
Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes |
| title_sort |
hypervalent iodine compounds for anti-markovnikov-type iodo-oxyimidation of vinylarenes |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2018-08-01 |
| description |
The iodo-oxyimidation of styrenes with the N-hydroxyimide/I2/hypervalent iodine oxidant system was proposed. Among the examined hypervalent iodine oxidants (PIDA, PIFA, IBX, DMP) PhI(OAc)2 proved to be the most effective; yields of iodo-oxyimides are 34–91%. A plausible reaction pathway includes the addition of an imide-N-oxyl radical to the double C=C bond and trapping of the resultant benzylic radical by iodine. It was shown that the iodine atom in the prepared iodo-oxyimides can be substituted by various nucleophiles. |
| topic |
free radicals hypervalent iodine imide-N-oxyl radicals iodination N-hydroxyimides oxidative functionalization |
| url |
https://doi.org/10.3762/bjoc.14.188 |
| work_keys_str_mv |
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