Recent Trends in Group 9 Catalyzed C-H Borylation Reactions: Different Strategies To Control Site-, Regio-, and Stereoselectivity
Recent Trends in Group 9 Catalyzed C-H Borylation Reactions: Different Strategies To Control Site-, Regio-, and Stereoselectivity
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DOI：
10.1055/a-1711-5889
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发表时间：
2022-01-18
影响因子：
2.6
通讯作者：
Dydio，Pawel
中科院分区：
文献类型：
--
作者：
Veth，Lukas;Grab，Hanusch A.;Dydio，Pawel
有机硼化合物继续为有机化学的进步做出重大贡献，其作为合成中间体和药物化学目标化合物的作用越来越大。它们的合成特别有吸引力的方法是基于可用起始材料的C-H键的直接硼化，因为不需要额外的预官能化步骤。然而，由于在有机分子中具有类似反应性的C-H键的高丰度，合成有用的C-H硼基化方案需要复杂的策略来实现高区域和立体选择性。为此，已经开发了选择性过渡金属基催化剂，其中第9族中心催化剂是最常用的。最近，已经开发了许多不同的策略来推动C-H硼化反应的区域和对映体选择性的边界。在此，我们提供了一个概述的方法，芳烃，烯烃和烷烃的C-H硼基化的基础上，第9族中心的催化剂，重点是最近的文献。最后，本文对该领域的未来潜力进行了展望。1引言1.1机理方面的考虑1.2 C-H硼化反应中的选择性问题1.3在C-H硼化反应中采用定向基团策略的不同作用模式1.4这篇简短评论的范围和目的2 C-H硼化反应的趋势2.1光诱导催化2.2转移C-H硼化2.3刘易斯酸介导的C-H硼化2.4定向金属化2.5杂类C-H硼化反应2.6静电相互作用2.7氢键3结论与展望
Organoboron compounds continue contributing substantially to advances in organic chemistry with their increasing role as both synthetic intermediates and target compounds for medicinal chemistry. Particularly attractive methods for their synthesis are based on the direct borylation of C–H bonds of available starting materials since no additional pre-functionalization steps are required. However, due to the high abundance of C–H bonds with similar reactivity in organic molecules, synthetically useful C–H borylation protocols demand sophisticated strategies to achieve high regio- and stereoselectivity. For this purpose, selective transition-metal-based catalysts have been developed, with group 9 centered catalysts being among the most commonly utilized. Recently, a multitude of diverse strategies has been developed to push the boundaries of C–H borylation reactions with respect to their regio- and enantioselectivity. Herein, we provide an overview of approaches for the C–H borylation of arenes, alkenes, and alkanes based on group 9 centered catalysts with a focus on the recent literature. Lastly, an outlook is given to assess the future potential of the field.1 Introduction1.1 Mechanistic Considerations1.2 Selectivity Issues in C–H Borylation1.3 Different Modes of Action Employing Directing Group Strategies in C–H Borylation1.4 Scope and Aim of this Short Review2 Trends in C–H Borylation Reactions2.1 Photoinduced Catalysis2.2 Transfer C–H Borylation2.3 Lewis Acid Mediated C–H Borylation2.4 Directed Metalation2.5 Miscellaneous C–H Borylation Reactions2.6 Electrostatic Interactions2.7 Hydrogen Bonding3 Conclusion and Outlook