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

Ikeda, Kazuki; Kojima, Riku; Kawai, Kentaro; Murakami, Takayasu; Kikuchi, Takashi; Kojima, Masahiro; Yoshino, Tatsuhiko; Matsunaga, Shigeki

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

Ikeda, Kazuki; Kojima, Riku; Kawai, Kentaro et al.

Journal of the American Chemical Society, 2023, 145(16), 9326-9333

Permalink : https://hdl.handle.net/2115/92021

このアイテムのアクセス数:291件（2026-01-23 11:28 集計）

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アクセス権	open access
URI	https://hdl.handle.net/2115/92021
タイトル	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
著者	Ikeda, Kazuki ; Kojima, Riku ; Kawai, Kentaro ; Murakami, Takayasu ; Kikuchi, Takashi ; Kojima, Masahiro ; Yoshino, Tatsuhiko ; Matsunaga, Shigeki
著者名 Ikeda, Kazuki
著者名 Kojima, Riku
著者名 Kawai, Kentaro
著者名 Murakami, Takayasu
著者名 Kikuchi, Takashi
e-Rad_Researcher 90824714 著者名 Kojima, Masahiro
e-Rad_Researcher 50756179 著者名 Yoshino, Tatsuhiko
e-Rad_Researcher 50334339 著者名 Matsunaga, Shigeki
言語	英語
発行日	2023-04-26
出版者	American Chemical Society
収録物名	Journal of the American Chemical Society
巻(号)	145(16)
ページ	9326-9333
抄録	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.
資源タイプ	学術雑誌論文
出版タイプ	Accepted Manuscript
権利情報	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.
PISSN	0002-7863
関連情報 (isVersionOf)	出版社版DOI https://doi.org/10.1021/jacs.3c02556