Diastereodivergent Synthesis of Vinylsilanes Using Solid Silylzinc Reagent

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-27 DOI:10.1021/acs.orglett.5c01814

Anirban Ganguly, Sundar Rajaraman, Venkadesh Balakrishnan and Ramesh Rasappan*,

引用次数: 0

Abstract

Vinylsilanes are extensively utilized in organic synthesis, especially in stereospecific reactions. Silylmetalation has emerged as a highly effective alternative to hydrosilylation; however, the silylcopper and silylzinc reagents used are generally obtained from pyrophoric silyllithium or disilanes. We describe a catalyst-controlled diastereodivergent hydrosilylation employing novel solid reagents that eliminates the need for pyrophoric silyl lithium and is free of detrimental lithium ions. Catalytic copper produced the E isomer, whereas the Z isomer was formed with stoichiometric iron.

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固体硅锌试剂非对映发散合成乙烯基硅烷。

乙烯基硅烷广泛应用于有机合成，特别是在立体定向反应中。硅金属化已成为硅氢化的高效替代品；然而，所用的硅铜和硅锌试剂通常是从焦性硅锂或二硅烷中获得的。我们描述了一种采用新型固体试剂的催化剂控制的非对映分散硅氢化反应，该反应消除了对焦性硅基锂的需要，并且不含有害的锂离子。催化铜生成E异构体，而化学计量铁生成Z异构体。

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.