Synthesis of vinylidenecyclopropanes via gold(i)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters

Hiroto Mori; Yusuke Ono; Shota Nakagawa; Sota Akima; Miki Murakami; Toshinobu Korenaga; Tadashi Nakaji-Hirabayashi; Mayumi Kyogoku; Yoshikazu Horino

doi:10.1039/d4cc04384g

Synthesis of vinylidenecyclopropanes via gold(i)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters

Hiroto Mori, Yusuke Ono, Shota Nakagawa, Sota Akima, Miki Murakami, Toshinobu Korenaga^*, Tadashi Nakaji-Hirabayashi, Mayumi Kyogoku, Yoshikazu Horino^*

^*この論文の責任著者

工学科　応用化学コース

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

1 被引用数 (Scopus)

抄録

The reaction of γ-stannylated propargyl esters in the presence of a cationic gold(i) catalyst affords vinylidenecyclopropane derivatives as a mixture of diastereomers. The cis-geometry of the alkenes is almost entirely retained in the product. DFT calculations suggest the involvement of the gold(i)-stabilized propargyl cation as a resonance form of gold(i)-coordinated allenylidene species.

本文言語	英語
ページ（範囲）	13518-13521
ページ数	4
ジャーナル	Chemical Communications
巻	60
号	92
DOI	https://doi.org/10.1039/d4cc04384g
出版ステータス	出版済み - 2024/10/07

ASJC Scopus 主題領域

電子材料、光学材料、および磁性材料
触媒
セラミックおよび複合材料
化学一般
表面、皮膜および薄膜
金属および合金
材料化学

文献へのアクセス

10.1039/d4cc04384g

フィンガープリント

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引用スタイル

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title = "Synthesis of vinylidenecyclopropanes via gold(i)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters",

abstract = "The reaction of γ-stannylated propargyl esters in the presence of a cationic gold(i) catalyst affords vinylidenecyclopropane derivatives as a mixture of diastereomers. The cis-geometry of the alkenes is almost entirely retained in the product. DFT calculations suggest the involvement of the gold(i)-stabilized propargyl cation as a resonance form of gold(i)-coordinated allenylidene species.",

author = "Hiroto Mori and Yusuke Ono and Shota Nakagawa and Sota Akima and Miki Murakami and Toshinobu Korenaga and Tadashi Nakaji-Hirabayashi and Mayumi Kyogoku and Yoshikazu Horino",

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doi = "10.1039/d4cc04384g",

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T1 - Synthesis of vinylidenecyclopropanes via gold(i)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters

AU - Mori, Hiroto

AU - Ono, Yusuke

AU - Nakagawa, Shota

AU - Akima, Sota

AU - Murakami, Miki

AU - Korenaga, Toshinobu

AU - Nakaji-Hirabayashi, Tadashi

AU - Kyogoku, Mayumi

AU - Horino, Yoshikazu

PY - 2024/10/7

Y1 - 2024/10/7

N2 - The reaction of γ-stannylated propargyl esters in the presence of a cationic gold(i) catalyst affords vinylidenecyclopropane derivatives as a mixture of diastereomers. The cis-geometry of the alkenes is almost entirely retained in the product. DFT calculations suggest the involvement of the gold(i)-stabilized propargyl cation as a resonance form of gold(i)-coordinated allenylidene species.

AB - The reaction of γ-stannylated propargyl esters in the presence of a cationic gold(i) catalyst affords vinylidenecyclopropane derivatives as a mixture of diastereomers. The cis-geometry of the alkenes is almost entirely retained in the product. DFT calculations suggest the involvement of the gold(i)-stabilized propargyl cation as a resonance form of gold(i)-coordinated allenylidene species.

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U2 - 10.1039/d4cc04384g

DO - 10.1039/d4cc04384g

M3 - 学術論文

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AN - SCOPUS:85207153189

SN - 1359-7345

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SP - 13518

EP - 13521

JO - Chemical Communications

JF - Chemical Communications

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