Methodologies and Strategies for Selective Borylation of C-Het and C-C Bonds.,Chemical Reviews

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Methodologies and Strategies for Selective Borylation of C-Het and C-C Bonds.
Chemical Reviews ( IF 51.4 ) Pub Date : 2020-06-29 , DOI: 10.1021/acs.chemrev.9b00384
Minyan Wang ₁ , Zhuangzhi Shi ₁

Affiliation

Organoborons have emerged as versatile building blocks in organic synthesis to achieve molecular diversity and as carboxylic acid bioisosteres with broad applicability in drug discovery. Traditionally, these compounds are prepared by the substitution of Grignard/lithium reagents with electrophilic boron species and Brown hydroboration. Recent developments have provided new routes for the efficient preparation of organoborons by applying reactions using chemical feedstocks with leaving groups. As compared to the previous methods that used organic halides (I, Br, and Cl), the direct borylation of less reactive C–Het and C–C bonds has become highly important to get efficiency and functional-group compatibility. This Review aims to provide a comprehensive overview of this topic, including (1) C–F bond borylation, (2) C–O bond borylation, (3) C–S bond borylation, (4) C–N bond borylation, and (5) C–C bond borylation. Considerable attention is given to the strategies and mechanisms involved. We expect that this Review will inspire chemists to discover more efficient transformations to expand this field.

中文翻译：

C-Het和CC键选择性硼化的方法和策略。

有机生物已成为有机合成中实现分子多样性的通用组成部分，并已成为在药物发现中具有广泛适用性的羧酸生物异构体。传统上，这些化合物是通过用亲电硼物种和布朗硼氢化取代格氏试剂/锂试剂制备的。最近的发展为使用带有离去基团的化学原料进行反应提供了有效制备有机硼的新途径。与以前使用有机卤化物（I，Br和Cl）的方法相比，反应性较低的C–Het和C–C键的直接硼化对于获得效率和官能团相容性已变得非常重要。这篇评论旨在对该主题进行全面概述，包括（1）C–F键硼化，（2）C–O键硼化，（3）C–S键硼化，（4）C–N键硼化，和（5）C–C键硼化。对所涉及的策略和机制给予了极大的关注。我们希望该评论会激发化学家发现更有效的转化方法以扩展该领域。

更新日期：2020-08-12

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