亚乙烯基环丙烷的合成：金（I）催化乙烯基芳烃与β-锡基炔丙基酯的环丙烷化反应

Synthesis of vinylidenecyclopropanes gold(I)-catalyzed cyclopropanation of vinyl arenes with -stannylated propargyl esters.

作者信息

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

机构信息

Department of Applied Chemistry and Bioscience, Chitose Institute of Science and Technology, Chitose, 066-8655, Japan.

Graduate School of Science and Engineering, University of Toyama, Toyama, 930-8555, Japan.

出版信息

Chem Commun (Camb). 2024 Nov 14;60(92):13518-13521. doi: 10.1039/d4cc04384g.

DOI:10.1039/d4cc04384g

PMID:39397684

Abstract

The reaction of -stannylated propargyl esters in the presence of a cationic gold(I) catalyst affords vinylidenecyclopropane derivatives as a mixture of diastereomers. The -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.

摘要

在阳离子金（I）催化剂存在下，-锡基炔丙基酯的反应生成了作为非对映异构体混合物的亚乙烯基环丙烷衍生物。烯烃的-构型在产物中几乎完全得以保留。密度泛函理论计算表明，金（I）稳定的炔丙基阳离子作为金（I）配位的亚丙二烯基物种的共振形式参与了反应。