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

Department of Fundamental Organic Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Journal	Synthesis (Germany)
DOIs	https://doi.org/10.1055/a-1818-0576
Publication status	Accepted/In press - 2022

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1055/a-1818-0576

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title = "3-Trifluoromethylbenzyne: Precise Orientation in Cycloaddition Reaction Enabled Regioselective Synthesis of Trifluoromethylated Triptycenes",

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",

language = "English",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

}

TY - JOUR

T1 - 3-Trifluoromethylbenzyne

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

N2 - 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.

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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DO - 10.1055/a-1818-0576

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JO - Synthesis

JF - Synthesis

SN - 0039-7881

ER -

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

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