Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound
An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-...
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| Format: | Article |
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MDPI AG
2019-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/6/1147 |
| _version_ | 1818519054582808576 |
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| author | Kazuhiro Watanabe Katsuhiko Moriyama |
| author_facet | Kazuhiro Watanabe Katsuhiko Moriyama |
| author_sort | Kazuhiro Watanabe |
| collection | DOAJ |
| description | An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indole derivatives as single regioisomers. <i>o</i>-Alkoxy(diacetoxyiodo)arenes showed higher reactivity in the reaction than <i>o</i>-alkyl(diacetoxyiodo)arenes, efficiently promoting the formation of indolyl(aryl)iodonium imides in the first step. |
| first_indexed | 2024-12-11T01:18:32Z |
| format | Article |
| id | doaj.art-5d5378b2e3774d2399256b04d9eaed77 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T01:18:32Z |
| publishDate | 2019-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5d5378b2e3774d2399256b04d9eaed772022-12-22T01:25:47ZengMDPI AGMolecules1420-30492019-03-01246114710.3390/molecules24061147molecules24061147Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine CompoundKazuhiro Watanabe0Katsuhiko Moriyama1Department of Chemistry, Graduate School of Science, and Molecular Chirality Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, JapanDepartment of Chemistry, Graduate School of Science, and Molecular Chirality Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, JapanAn oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxidative C–N coupling reaction to obtain 3-amino indole derivatives as single regioisomers. <i>o</i>-Alkoxy(diacetoxyiodo)arenes showed higher reactivity in the reaction than <i>o</i>-alkyl(diacetoxyiodo)arenes, efficiently promoting the formation of indolyl(aryl)iodonium imides in the first step.https://www.mdpi.com/1420-3049/24/6/1147<i>o</i>-substituted iodoareneindoleCu catalystC–N coupling reactionhypervalent iodineone-pot reactionregioselectivity |
| spellingShingle | Kazuhiro Watanabe Katsuhiko Moriyama Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound Molecules <i>o</i>-substituted iodoarene indole Cu catalyst C–N coupling reaction hypervalent iodine one-pot reaction regioselectivity |
| title | Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound |
| title_full | Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound |
| title_fullStr | Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound |
| title_full_unstemmed | Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound |
| title_short | Cu-Catalyzed Oxidative 3-Amination of Indoles via Formation of Indolyl(aryl)iodonium Imides Using <i>o</i>-Substituted (Diacetoxyiodo)arene as a High-Performance Hypervalent Iodine Compound |
| title_sort | cu catalyzed oxidative 3 amination of indoles via formation of indolyl aryl iodonium imides using i o i substituted diacetoxyiodo arene as a high performance hypervalent iodine compound |
| topic | <i>o</i>-substituted iodoarene indole Cu catalyst C–N coupling reaction hypervalent iodine one-pot reaction regioselectivity |
| url | https://www.mdpi.com/1420-3049/24/6/1147 |
| work_keys_str_mv | AT kazuhirowatanabe cucatalyzedoxidative3aminationofindolesviaformationofindolylaryliodoniumimidesusingioisubstituteddiacetoxyiodoareneasahighperformancehypervalentiodinecompound AT katsuhikomoriyama cucatalyzedoxidative3aminationofindolesviaformationofindolylaryliodoniumimidesusingioisubstituteddiacetoxyiodoareneasahighperformancehypervalentiodinecompound |