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Formation of Isolable Dearomatized [4+2] Cycloadducts from Benzenes, Naphthalenes, and N-Heterocycles Using 1,2-Dihydro-1,2,4,5-tetrazine-3,6-diones as Arenophiles under Visible Light Irradiation
| Title: | Formation of Isolable Dearomatized [4+2] Cycloadducts from Benzenes, Naphthalenes, and N-Heterocycles Using 1,2-Dihydro-1,2,4,5-tetrazine-3,6-diones as Arenophiles under Visible Light Irradiation |
| Authors: | Ikeda, Kazuki Browse this author | | Kojima, Riku Browse this author | | Kawai, Kentaro Browse this author | | Murakami, Takayasu Browse this author | | Kikuchi, Takashi Browse this author | | Kojima, Masahiro Browse this author →KAKEN DB | | Yoshino, Tatsuhiko Browse this author →KAKEN DB | | Matsunaga, Shigeki Browse this author →KAKEN DB |
| Issue Date: | 26-Apr-2023 |
| Publisher: | American Chemical Society |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 145 |
| Issue: | 16 |
| Start Page: | 9326 |
| End Page: | 9333 |
| Publisher DOI: | 10.1021/jacs.3c02556 |
| Abstract: | We report that the dearomative [4 + 2] cycloaddition between 1,2-dihydro-1,2,4,5-tetrazine-3,6-diones (TETRADs) and benzenes, naphthalenes, or N-heteroaromatic compounds under visible light irradiation affords the corresponding isolable cycloadducts. Several synthetic transformations including transition-metal-catalyzed allylic substitution reactions using the isolated cycloadducts at room temperature or above were demonstrated. Computational studies revealed that the retro-cycloaddition of the benzene-TETRAD adduct proceeds via an asynchronous concerted mechanism, while that of the benzene-MTAD adduct (MTAD = 4-methyl-1,2,4-triazoline-3,5-dione) proceeds via a synchronous mechanism. |
| Rights: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/articlesonrequest/AOR-RBIKUHCVTHAZKHSA3M2A. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/92021 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 吉野 達彦
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