芳烃间/对位选择性碳氢硼化反应研究进展

doi:10.6023/cjoc202302022

摘要/Abstract

有机硼化物是实现分子多样性的重要砌块, 通过碳氢硼化将碳氢化合物转化为有机硼化物的策略非常具有吸引力. 其中铱催化的碳氢硼化取得了重大进展. 由于取代芳烃通常含有邻位、间位和对位的碳氢键, 因此区域选择控制一直是芳香族碳氢硼化的一个长期挑战. 在过去十年中, 邻位选择性碳氢硼化取得了重大进展, 而间位和对位选择性依然具有挑战性. 这篇综述旨在对铱催化的间/对选择性芳香族碳氢硼化反应提供一份详尽的总结, 从导向和非导向碳氢硼化两个角度进行梳理.

关键词: 间位选择性, 对位选择性, 铱催化, 碳氢硼化, 导向基团

Organoboron compounds are important building blocks to create molecular diversity. Strategies that can transform the readily available hydrocarbons into these compounds by C—H borylation are highly attractive. In this context, significant progress has been made towards iridium-catalyzed C—H borylation. Because substituted arenes typically contain ortho-, meta- and para-C—H bonds, regiocontrol has been a long-standing challenge within this type of chemistry. During the past decade, significant progress has been made in the ortho-selective C—H borylation, while the meta-/para-selectivity is still challenging. This review aims to provide a comprehensive overview of this topic on meta-/para-selective aromatic C—H borylation by iridium catalysis. This topic is categorized into directed and non-directed C—H borylation.

Key words: meta selectivity, para selectivity, iridium catalysis, C—H borylation, directing groups

引用此文

蒋旺, 史壮志. 芳烃间/对位选择性碳氢硼化反应研究进展[J]. 有机化学, 2023, 43(5): 1691-1705.

Wang Jiang, Zhuangzhi Shi. Recent Progress in meta-/para-Selective Aromatic C—H Borylation[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1691-1705.

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图/表 19

图式1. 芳环间位和对位碳氢硼化的策略

Scheme 1. General strategies for meta- and para-selective C—H borylation of arenes

图式2. 氢键诱导芳香酰胺间位碳氢硼化

Scheme 2. meta-Selective C—H borylation of aromatic amides via hydrogen bonds

图式3. 氢键协助苄胺/苯乙胺/苯丙胺间位碳氢硼化

Scheme 3. meta-Selective C—H borylation of benzylic amines/phenylethylamine/amphetamine via hydrogen bonds

图式4. 氢键协助苄胺间位不对称碳氢硼化

Scheme 4. Asymmetric meta-selective C—H borylation of benzylic amines via hydrogen bonds

图式5. 计算机辅助设计配体实现芳环远端碳氢可控硼化

Scheme 5. Computationally designed ligands enable tunable borylation of remote C—H bonds in arenes

图式6. 氢键协助磺酰芳烃的间/对选择性碳氢硼化

Scheme 6. Controlled meta-/para-selective C—H borylation of aryl sulfonyl compounds via hydrogen bonds

图式7. 静电作用协助酰基芳胺间位碳氢硼化

Scheme 7. meta-Selective C—H borylation of acyl aromatic amines via electrostatic interactions

图式8. 氮硼配位协助芳香醛间位碳氢硼化

Scheme 8. meta-Selective C—H borylation of aromatic aldehyde via B—N coordination

图式9. 配位作用协助吡啶间位碳氢硼化

Scheme 9. meta-Selective C—H borylation of pyridines via coordination

图式10. 离子对协助间位碳氢硼化

Scheme 10. Ion-pair assisted meta-selective C—H borylation

图式11. 芳香酰胺的间位碳氢硼化和芳香酯的对位碳氢硼化

Scheme 11. meta-/para-Selective C—H borylation of aromatic amide/aromatic esters

图式12. 酰胺和吡啶的间位选择性硼化

Scheme 12. meta-Selective borylation of amide and pyridine

图式13. 离子对协助芳香季铵盐间位碳氢硼化

Scheme 13. Ion-pair assisted meta-selective C—H borylation aromatic quaternary ammonium salt

图式14. 双膦配体实现芳烃对位选择性硼化

Scheme 14. para-Selective borylation of aromatics by diphosphate ligands

图式15. 芳烃的间位选择性硼化

Scheme 15. meta-Selective borylation of aromatic hydrocarbons

图式16. N-Boc酰胺的对位选择性硼化

Scheme 16. para-Selective borylation of N-Boc amide

图式17. 铝路易斯酸协助的对位选择性硼化

Scheme 17. para-Selective borylation assisted by aluminum lewis acid

图式18. 离子对协助的对位选择性硼化

Scheme 18. Ion-pair assisted para-selective borylation

图式19. 芳胺的对位选择性硼化

Scheme 19. para-Selective borylation of aromatic amines

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