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^*

^*Corresponding author for this work

Applied Chemistry

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

1 Scopus citations

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.

Original language	English
Pages (from-to)	13518-13521
Number of pages	4
Journal	Chemical Communications
Volume	60
Issue number	92
DOIs	https://doi.org/10.1039/d4cc04384g
State	Published - 2024/10/07

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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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

C2 - 39397684

AN - SCOPUS:85207153189

SN - 1359-7345

VL - 60

SP - 13518

EP - 13521

JO - Chemical Communications

JF - Chemical Communications

IS - 92

ER -

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

Abstract

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