氢原子转移介导的烷烃C(sp3)—H选择性官能团化研究进展

doi:10.6023/cjoc202407027

摘要/Abstract

作为一种高度原子经济性和步骤经济性的策略, 通过烷烃C(sp³)—H键的官能团化, 直接将烷烃转化成附加值更高的化学品, 一直备受关注. 然而由于烷烃C(sp³)—H键广为人知的惰性, 控制非活化C(sp³)—H键官能团化的化学选择性和区域选择性是一项重大的挑战. 作为一种近期重新引起关注的方法, 相比以往过渡金属催化, 利用氢原子转移(HAT)实现C(sp³)—H键选择性官能团化有着其独特之处. 在此, 对最近兴起的各种HAT介导的非活化C(sp³)—H键官能团化的方法进行了分析, 按照官能团化的选择性分类, 重点介绍了目前实现区域选择性控制的方法. 最后总结了目前方法的局限性, 并对这一领域当前的挑战和未来的发展方向进行了展望.

关键词: 氢原子转移, 非活化C(sp³)—H键, C(sp³)—H键官能团化, 区域选择性, 烷烃

As a highly atom-economical and step-economic strategy, the functionalization of alkane C(sp³)—H bonds to directly convert alkanes into higher value-added chemicals has been a subject of great interest. However, due to the well-known inertness of alkane C(sp³)—H bonds, controlling the chemical selectivity and regioselectivity of non-activated C(sp³)—H bond functionalization poses a significant challenge. Recently, the utilization of hydrogen atom transfer (HAT) for achieving selectivity in C(sp³)—H bond functionalization has attracted renewed attention as a method distinct from traditional transition metal-catalyzed approaches. Herein, various HAT-mediated non-activated C(sp³)—H bond functionalization methods are analyzed based on selectivity of functionalization with a focus on methods that have achieved regioselectivity control. The current limitations of existing methods are summarized and the current challenges and future directions in this field are outlooked.

Key words: hydrogen atom transfer, unactivated C(sp³)—H bond, C(sp³)—H functionalization, regioselectivity, alkane

引用此文

王淼, 黄雅豪, 胡鹏. 氢原子转移介导的烷烃C(sp³)—H选择性官能团化研究进展[J]. 有机化学, 2025, 45(2): 477-497.

Miao Wang, Yahao Huang, Peng Hu. Recent Advances in Hydrogen Atom Transfer Induced Selective C(sp³)—H Functionalization of Alkanes[J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 477-497.

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图/表 25

图1. (a)烷烃的HAT与自由基官能团化、(b) HAT转移过程、(c)烷烃C(sp3)—H键性质对HAT的影响、(d)自由基官能团化过程、(e)自由基性质对官能团化步骤的影响及(f) HAT介导的自由基官能团化文献数量

Figure 1. (a) HAT of alkanes and radical functionalization, (b) process of HAT, (c) impact of alkane C(sp3)—H bond properties on HAT, (d) process of radical functionalization, (e) impact of radical properties on the functionalization, and (f) number of documents on HAT induced radical functionalization

图式1. HAT介导的3° C(sp3)—H键选择性官能团化示例

Scheme 1. Examples of HAT-induced selective functionalization of 3° C(sp3)—H bonds

图式2. 氯自由基的产生方式与氯自由基介导的非选择性官能团化示例

Scheme 2. Methods of generating chlorine radicals and examples of non-selective functionalization induced by chlorine radicals

图式3. 氯自由基复合物介导的3° C(sp3)—H键选择性官能团化示例

Scheme 3. Examples of chlorine radical complex-induced selective functionalization of 3° C(sp3)—H bonds

图式4. 溴自由基介导的3° C(sp3)—H键选择性官能团化

Scheme 4. Bromine radical-induced selective functionalization of 3° C(sp3)—H bonds

图式5. 烷氧自由基介导的3° C(sp3)—H键选择性官能团化

Scheme 5. Alkoxyl radical induced selective functionalization of 3° C(sp3)—H bonds

图式6. 羧基自由基介导的3° C(sp3)—H键选择性官能团化

Scheme 6. Carboxyl radicals induced selective functionalization of 3° C(sp3)—H bonds

图式7. 曙红Y介导的3° C(sp3)—H键选择性官能团化

Scheme 7. Eosin Y induced selective functionalization of 3° C(sp3)—H bonds

图式8. 吡啶氮氧化物介导的3° C(sp3)—H键选择性官能团化

Scheme 8. Pyridine N-oxide-induced selective functionalization of 3° C(sp3)—H bonds

图式9. DABCO介导的3° C(sp3)—H键选择性官能团化

Scheme 9. DABCO induced selective functionalization of 3° C(sp3)—H bonds

图式10. 硫自由基介导HAT的竞争过程

Scheme 10. Competitive processes of HAT induced by sulfur radical

图式11. 四氟吡啶硫自由基介导的3° C(sp3)—H键选择性官能团化

Scheme 11. Tetrafluoropyridine sulfur radical-induced selective functionalization of 3° C(sp3)—H bonds

图式12. 四氮唑硫自由基介导的3° C(sp3)—H键选择性官能团化

Scheme 12. Tetrazole sulfur radical-induced selective functionalization of 3° C(sp3)—H bonds

图式13. 氯气阴离子自由基介导的2° C(sp3)—H键选择性官能团化

Scheme 13. Chlorine anion radical-induced selective functionalization of 2° C(sp3)—H bonds

图式14. TBADT介导的2° C(sp3)—H键选择性官能团化

Scheme 14. TBADT-induced selective functionalization of 2° C(sp3)—H bonds

图式15. 羧基自由基介导的2° C(sp3)—H键选择性官能团化

Scheme 15. Carboxyl radical-induced selective functionalization of 2° C(sp3)—H bonds

图式16. 氮阳离子自由基对直链烷烃C(sp3)—H键氯代的选择性调控

Scheme 16. Selective C(sp3)—H chlorination of linear alkanes regulated by nitrogen cation radicals

图式17. 氮阳离子自由基介导的2° C(sp3)—H键选择性官能团化

Scheme 17. Nitrogen cation radical-induced selective functionalization of 2° C(sp3)—H bonds

图式18. 氮自由基介导的2° C(sp3)—H键选择性官能团化

Scheme 18. Nitrogen radical-induced selective functionalization of 2° C(sp3)—H bonds

图式19. 酰胺氮自由基对C(sp3)—H键官能团化选择性调控

Scheme 19. Amide nitrogen radical-induced selectivity control of C(sp3)—H bond functionalization

图式20. 氯自由基复合物介导的1° C(sp3)—H键选择性官能团化

Scheme 20. Chlorine radical complex-induced selective functionalization of 1° C(sp3)—H bonds

图式21. 氯自由基复合物介导的1° C(sp3)—H键选择性硼基化

Scheme 21. Chlorine radical complex-induced selective borylation of 1° C(sp3)—H bonds

图式22. HAT介导的1° C(sp3)—H键选择性硼基化的不同机理

Scheme 22. Different mechanisms of HAT induced selective 1° C(sp3)—H borylation

图式23. HAT介导的直链烷烃1° C(sp3)—H键选择性硼基化

Scheme 23. HAT induced selective 1° C(sp3)—H borylation of linear alkanes

图式24. HAT介导的选择性官能团化特例

Scheme 24. Special cases of HAT induced selective C(sp3)—H functionalization

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氢原子转移介导的烷烃C(sp³)—H选择性官能团化研究进展

Recent Advances in Hydrogen Atom Transfer Induced Selective C(sp³)—H Functionalization of Alkanes

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