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

doi:10.6023/cjoc202407027

Abstract

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

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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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Fig. & Tab. 25

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

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

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

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

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

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

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

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

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

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

Scheme 10. Competitive processes of HAT induced by sulfur radical

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

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

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

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

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

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

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

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

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

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

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

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

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

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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氢原子转移介导的烷烃C(sp3)—H选择性官能团化研究进展