3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes

Takayuki Iwata; Mizuki Hyodo; Takumi Fujiwara; Ryusei Kawano; Leah Kuhn; Igor V. Alabugin; Mitsuru Shindo

doi:10.1055/a-1818-0576

3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes

Takayuki Iwata, Mizuki Hyodo, Takumi Fujiwara, Ryusei Kawano, Leah Kuhn, Igor V. Alabugin, Mitsuru Shindo

物質基盤化学部門

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

2 被引用数 (Scopus)

抄録

The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. Triple cycloaddition of ynolates to the benzyne provided 1,8,13-tris(trifluoromethyl)triptycenes with high regioselectivity. 1-Trifluoromethyltriptycenes were regioselectively obtained by the Diels-Alder reaction of anthranoxides with the benzyne. These selectivities are attributed to the electron-acceptor nature of the trifluoromethyl group on the benzyne.

本文言語	英語
ジャーナル	Synthesis (Germany)
DOI	https://doi.org/10.1055/a-1818-0576
出版ステータス	印刷中 - 2022

!!!All Science Journal Classification (ASJC) codes

触媒
有機化学

文献へのアクセス

10.1055/a-1818-0576

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引用スタイル

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abstract = "The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. Triple cycloaddition of ynolates to the benzyne provided 1,8,13-tris(trifluoromethyl)triptycenes with high regioselectivity. 1-Trifluoromethyltriptycenes were regioselectively obtained by the Diels-Alder reaction of anthranoxides with the benzyne. These selectivities are attributed to the electron-acceptor nature of the trifluoromethyl group on the benzyne.",

author = "Takayuki Iwata and Mizuki Hyodo and Takumi Fujiwara and Ryusei Kawano and Leah Kuhn and Alabugin, {Igor V.} and Mitsuru Shindo",

year = "2022",

doi = "10.1055/a-1818-0576",

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T2 - Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes

AU - Iwata, Takayuki

AU - Hyodo, Mizuki

AU - Fujiwara, Takumi

AU - Kawano, Ryusei

AU - Kuhn, Leah

AU - Alabugin, Igor V.

AU - Shindo, Mitsuru

PY - 2022

Y1 - 2022

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AB - The first regioselective addition reactions to 3-trifluoromethylbenzyne are reported. Triple cycloaddition of ynolates to the benzyne provided 1,8,13-tris(trifluoromethyl)triptycenes with high regioselectivity. 1-Trifluoromethyltriptycenes were regioselectively obtained by the Diels-Alder reaction of anthranoxides with the benzyne. These selectivities are attributed to the electron-acceptor nature of the trifluoromethyl group on the benzyne.

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