Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with Indoles
C3–N1′ bond formation of bisindoles has been a great challenge due to the intrinsic reactivity of indoles as both C3 and N1-nucleophilic character. Herein, we demonstrate an C3–N1′ cross-coupling reaction of indoles using <i>N</i>-methoxyindoles as N-electrophilic indole reagents in the...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-03-01
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| Series: | Chemistry |
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| Online Access: | https://www.mdpi.com/2624-8549/5/1/33 |
| _version_ | 1797612884890484736 |
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| author | Keisuke Tokushige Toshiki Yamashiro Seiya Hirao Takumi Abe |
| author_facet | Keisuke Tokushige Toshiki Yamashiro Seiya Hirao Takumi Abe |
| author_sort | Keisuke Tokushige |
| collection | DOAJ |
| description | C3–N1′ bond formation of bisindoles has been a great challenge due to the intrinsic reactivity of indoles as both C3 and N1-nucleophilic character. Herein, we demonstrate an C3–N1′ cross-coupling reaction of indoles using <i>N</i>-methoxyindoles as N-electrophilic indole reagents in the presence of Lewis acid. The bisindoles generated in this transformation are latent C3-nucleophile, allowing them to be used as strategic intermediates in sequential C3–N1′–C3′–N1″ triindole formations. The potential synthetic usefulness of this sequential transformation was highlighted upon application to the construction of C3–N1 looped polyindoles. |
| first_indexed | 2024-03-11T06:47:11Z |
| format | Article |
| id | doaj.art-efe7a63d0b79492f992d6686f7c1770f |
| institution | Directory Open Access Journal |
| issn | 2624-8549 |
| language | English |
| last_indexed | 2024-03-11T06:47:11Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry |
| spelling | doaj.art-efe7a63d0b79492f992d6686f7c1770f2023-11-17T10:15:47ZengMDPI AGChemistry2624-85492023-03-015145246210.3390/chemistry5010033Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with IndolesKeisuke Tokushige0Toshiki Yamashiro1Seiya Hirao2Takumi Abe3Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Okayama City 700-8530, JapanGraduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Okayama City 700-8530, JapanGraduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Okayama City 700-8530, JapanGraduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Okayama City 700-8530, JapanC3–N1′ bond formation of bisindoles has been a great challenge due to the intrinsic reactivity of indoles as both C3 and N1-nucleophilic character. Herein, we demonstrate an C3–N1′ cross-coupling reaction of indoles using <i>N</i>-methoxyindoles as N-electrophilic indole reagents in the presence of Lewis acid. The bisindoles generated in this transformation are latent C3-nucleophile, allowing them to be used as strategic intermediates in sequential C3–N1′–C3′–N1″ triindole formations. The potential synthetic usefulness of this sequential transformation was highlighted upon application to the construction of C3–N1 looped polyindoles.https://www.mdpi.com/2624-8549/5/1/331′<i>H</i>-1,3′-biindoleN-electrophilic<i>N</i>-methoxyindolesbisindolesaluminumcross-coupling |
| spellingShingle | Keisuke Tokushige Toshiki Yamashiro Seiya Hirao Takumi Abe Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with Indoles Chemistry 1′<i>H</i>-1,3′-biindole N-electrophilic <i>N</i>-methoxyindoles bisindoles aluminum cross-coupling |
| title | Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with Indoles |
| title_full | Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with Indoles |
| title_fullStr | Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with Indoles |
| title_full_unstemmed | Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with Indoles |
| title_short | Aluminum-Catalyzed Cross Selective C3–N1′ Coupling Reactions of <i>N</i>-Methoxyindoles with Indoles |
| title_sort | aluminum catalyzed cross selective c3 n1 coupling reactions of i n i methoxyindoles with indoles |
| topic | 1′<i>H</i>-1,3′-biindole N-electrophilic <i>N</i>-methoxyindoles bisindoles aluminum cross-coupling |
| url | https://www.mdpi.com/2624-8549/5/1/33 |
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