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Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes
The iodo-oxyimidation of styrenes with the N-hydroxyimide/I(2)/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...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2018
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122379/ https://www.ncbi.nlm.nih.gov/pubmed/30202467 http://dx.doi.org/10.3762/bjoc.14.188 |
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| author | Krylov, Igor B Paveliev, Stanislav A Syroeshkin, Mikhail A Korlyukov, Alexander A Dorovatovskii, Pavel V Zubavichus, Yan V Nikishin, Gennady I Terent’ev, Alexander O |
| author_facet | Krylov, Igor B Paveliev, Stanislav A Syroeshkin, Mikhail A Korlyukov, Alexander A Dorovatovskii, Pavel V Zubavichus, Yan V Nikishin, Gennady I Terent’ev, Alexander O |
| author_sort | Krylov, Igor B |
| collection | PubMed |
| description | The iodo-oxyimidation of styrenes with the N-hydroxyimide/I(2)/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. |
| format | Online Article Text |
| id | pubmed-6122379 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-61223792018-09-10 Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes Krylov, Igor B Paveliev, Stanislav A Syroeshkin, Mikhail A Korlyukov, Alexander A Dorovatovskii, Pavel V Zubavichus, Yan V Nikishin, Gennady I Terent’ev, Alexander O Beilstein J Org Chem Full Research Paper The iodo-oxyimidation of styrenes with the N-hydroxyimide/I(2)/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. Beilstein-Institut 2018-08-16 /pmc/articles/PMC6122379/ /pubmed/30202467 http://dx.doi.org/10.3762/bjoc.14.188 Text en Copyright © 2018, Krylov et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Krylov, Igor B Paveliev, Stanislav A Syroeshkin, Mikhail A Korlyukov, Alexander A Dorovatovskii, Pavel V Zubavichus, Yan V Nikishin, Gennady I Terent’ev, Alexander O Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes |
| title | 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_short | Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes |
| title_sort | hypervalent iodine compounds for anti-markovnikov-type iodo-oxyimidation of vinylarenes |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122379/ https://www.ncbi.nlm.nih.gov/pubmed/30202467 http://dx.doi.org/10.3762/bjoc.14.188 |
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