Geng Shasha, Pu Yu, Wang Siyu, Ji Yanru, Feng Zhang
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.
Sichuan Key Laboratory of Medical Imaging, North Sichuan Medical College, Nanchong, Sichuan 637000, P. R. China.
Chem Commun (Camb). 2024 Mar 26;60(26):3484-3506. doi: 10.1039/d4cc00288a.
Organosilane compounds are widely used in both organic synthesis and materials science. Particularly, 1,2-disilylated and -disilylated alkenes, characterized by a carbon-carbon double bond and multiple silyl groups, exhibit significant potential for subsequently diverse transformations. The versatility of these compounds renders them highly promising for applications in materials, enabling them to be valuable and versatile building blocks in organic synthesis. This review provides a comprehensive summary of methods for the preparation of /-1,2-disilylated and -disilylated alkenes. Despite notable advancements in this field, certain limitations persist, including challenges related to regioselectivity in the incorporation and chemoselectivity in the transformation of two nearly identical silyl groups. The primary objective of this review is to outline synthetic methodologies for the generation of these alkenes through disilylation reactions, employing silicon reagents, specifically disilanes, hydrosilanes, and silylborane reagents. The review places particular emphasis on investigating the practical applications of the C-Si bond of disilylalkenes and delves into an in-depth discussion of reaction mechanisms, particularly those reactions involving the activation of Si-Si, Si-H, and Si-B bonds, as well as the C-Si bond formation.
有机硅烷化合物在有机合成和材料科学中都有广泛应用。特别是，具有碳 - 碳双键和多个硅烷基的1,2 - 二硅基化和 - 二硅基化烯烃在随后的多种转化中展现出巨大潜力。这些化合物的多功能性使其在材料应用方面极具前景，使它们成为有机合成中有价值且通用的构建单元。本综述全面总结了制备 / - 1,2 - 二硅基化和 - 二硅基化烯烃的方法。尽管该领域取得了显著进展，但仍存在某些局限性，包括在两个几乎相同的硅烷基的引入中区域选择性以及转化中的化学选择性方面的挑战。本综述的主要目的是概述通过二硅基化反应，使用硅试剂，特别是乙硅烷、硅烷和甲硅烷基硼烷试剂生成这些烯烃的合成方法。该综述特别强调研究二硅基烯烃的C - Si键的实际应用，并深入讨论反应机理，特别是那些涉及Si - Si、Si - H和Si - B键活化以及C - Si键形成的反应。
