| ID | 63100 |
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| Author |
Yamashiro, Toshiki
Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
Abe, Takumi
Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
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Tanioka, Masaru
School of Pharmaceutical Sciences, Aichi Gakuin University
Kamino, Shinichiro
School of Pharmaceutical Sciences, Aichi Gakuin University
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Sawada, Daisuke
Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
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| Abstract | Use of 3-azidoindoles in organic synthesis remains a difficult task owing to their instabilities. Herein, we report a general and concise approach for tackling this problem by using 3-azidoindole surrogates. The surrogates are bench-stable, presumably due to the observed intramolecular O-N-beta bonding. The resultant fleeting intermediates undergo capturing in situ to afford 3-substitued indoles through formal ipso-substitution of the azide group by nucleophiles. In these investigations, we found that the fleeting 3-azidoindoles show a C3-electrophilic character for the first time.
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| Note | This is an Accepted Manuscript of an article published by Royal Society of Chemistry.
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| Published Date | 2021-11-16
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| Publication Title |
Chemical Communications
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| Volume | volume57
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| Publisher | Royal Society of Chemistry (RSC)
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| Start Page | 13381
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| End Page | 13384
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| ISSN | 1359-7345
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| NCID | AA11071130
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| Content Type |
Journal Article
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| language |
English
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| OAI-PMH Set |
岡山大学
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| Copyright Holders | © The Royal Society of Chemistry 2021
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| File Version | author
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| Related Url | isVersionOf https://doi.org/10.1039/d1cc06033c
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