Copper-Catalyzed Stereoconvergent 1,4-Protosilylation of E/Z Dienes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-02 DOI:10.1021/acs.orglett.5c01841

Longtao Huang, Yueyuan Wang, Min Gao, Shizhao Xu, Luqing Lin

引用次数: 0

Abstract

The conversion of E/Z isomeric olefin mixtures to a singular product is both significant and challenging. In this study, we present a copper-catalyzed stereoconvergent 1,4-protosilylation of E/Z conjugated diene mixtures, yielding allylic silanes with exclusive 1,4-regioselectivity and a Z configuration. Density functional theory (DFT) calculations indicate stereoconvergent 1,4-protosilylation through Zimmerman–Traxler transition states during the protonation step, leading to the formation of the final Z isomer, allylic silane.

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铜催化E/Z二烯的立体聚合1,4-原硅基化反应

将E/Z同分异构体烯烃混合物转化为单一产物既重要又具有挑战性。在这项研究中，我们提出了铜催化的E/Z共轭二烯混合物的立体收敛1,4-原硅基化反应，得到了具有独家1,4区域选择性和Z构型的烯丙基硅烷。密度泛函理论（DFT）计算表明，在质子化步骤中，通过Zimmerman-Traxler过渡态，立体会聚1,4-原硅基化，最终形成Z异构体，烯丙基硅烷。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.