Recent Advances in Transition Metal-Catalyzed Radical-Mediated Selective Difunctionalization of 1,3-Dienes

doi:10.6023/cjoc202512029

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (4): 1330-1359.DOI: 10.6023/cjoc202512029 Previous Articles Next Articles

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过渡金属催化自由基介导1,3-二烯的选择性双官能团化研究进展

刘水林^a, 陈镤^a^,^*(), 贺晶^a, 刘宁^a^,^*(), 黄华文^b^,^c^,^*()

^a 湖南工学院化学与环境工程学院湖南衡阳 421200
^b 湘潭大学化学学院湖南湘潭 411100
^c 河南师范大学化学化工学院河南新乡 453007

收稿日期:2025-12-29 修回日期:2026-01-26 发布日期:2026-03-20
通讯作者: 陈镤, 刘宁, 黄华文
基金资助:
国家自然科学基金(22071211); 湖南省教育厅重点项目(22A0631); 湖南省教育厅重点项目(22A0628); 湖南省自然科学基金区域联合项目(2025JJ70140); 及湖南省大学生创新创业训练计划(S202511528219S)

Recent Advances in Transition Metal-Catalyzed Radical-Mediated Selective Difunctionalization of 1,3-Dienes

Shuilin Liu^a, Pu Chen^a^,^*(), Jing He^a, Ning Liu^a^,^*(), Huawen Huang^b^,^c^,^*()

^a College of Chemistry and Environmental Engineering, Hunan Institute of Technology, Hengyang, Hunan 421200
^b College of Chemistry, Xiangtan University, Xiangtan, Hunan 411100
^c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2025-12-29 Revised:2026-01-26 Published:2026-03-20
Contact: Pu Chen, Ning Liu, Huawen Huang
Supported by:
National Natural Science Foundation of China(22071211); Key Projects of Hunan Provincial Department of Education(22A0631); Key Projects of Hunan Provincial Department of Education(22A0628); Regional Joint Project of Hunan Provincial Natural Science Foundation(2025JJ70140); Hunan Provincial College Students’ Innovative Entrepreneurship Training Program Project(S202511528219S)

In recent years, the rapid advancement of radical chemistry and its deep integration with transition metal catalysis have established a powerful new paradigm for the efficient construction of complex molecules in organic synthesis. Compared with traditional ionic reactions, radical reactions offer unique advantages such as mild reaction conditions, good functional group compatibility, and the ability to rapidly build molecular complexity, which have garnered sustained attention from synthetic chemists. 1,3-Dienes, as a class of readily available and structurally diverse building blocks, are widely embedded in natural products and functional molecules, and their selective difunctionalization remains a significant challenge and an active area of research. Radical-based strategies, particularly when synergized with transition metal catalysis, not only overcome the limitations of conventional polar reactivity, but also unlock novel chemical space, enabling the one-pot, simultaneous incorporation of two distinct functional groups to afford high-value allylic compounds with precision. A systematic overview of key advances over the past three years is provided. Emphasis is placed on the development of diverse transition metal catalysts, innovative radical precursors, evolving mechanistic understanding, and representative catalytic systems. Through illustrative examples, their synthetic applications and future potential are further discussed, aiming to offer both conceptual insights and practical guidance to inspire continued innovation in this dynamic field.

Key words: transition metal catalysis, radical, 1,3-diene, difunctionalization, selectivity

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Shuilin Liu, Pu Chen, Jing He, Ning Liu, Huawen Huang. Recent Advances in Transition Metal-Catalyzed Radical-Mediated Selective Difunctionalization of 1,3-Dienes[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1330-1359.

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Fig. & Tab. 53

Figure 1. Summary of radical-mediated 1,3-diene reactions

Scheme 1. Copper-catalyzed asymmetric 1,2-alkylesterification of 1,3-dienes

Scheme 2. Copper-catalyzed asymmetric 1,2-carbocyanation of 1,3-dienes

Scheme 3. Copper/silver co-catalyzed 1,2-aminofluorination of 1,3-dienes

Scheme 4. Photo-induced copper-catalyzed 1,2-aminoesterification of 1,3-dienes

Scheme 5. Photo-induced copper-catalyzed 1,2-azidoesterification of 1,3-dienes

Scheme 6. Copper-catalyzed 1,2-dioxygenation of 1,3-dienes

Scheme 7. Copper-catalyzed 1,2-phosphonoazidation of 1,3-dienes

Scheme 8. Copper-catalyzed 1,2-sulfone etherification of 1,3-dienes

Scheme 9. Copper-catalyzed 1,2-selenide etherification/amination of 1,3-dienes

Scheme 10. Copper-catalyzed selective 1,4- or 1,2-carboamination of 1,3-dienes

Scheme 11. Copper-catalyzed 1,4-carboamination of 1,3-dienes

Scheme 12. Copper-catalyzed asymmetric 1,4-perfluoroalkylamination of 1,3-dienes

Scheme 13. Copper-catalyzed 1,4-sulfonyl indolylation of 1,3-dienes

Scheme 14. Copper-catalyzed Heck functionalization of 1,3-dienes with sulfonyl chloride

Scheme 15. Photo-induced palladium-catalyzed asymmetric 1,2-carboamination of 1,3-dienes

Scheme 16. Photo-induced palladium-catalyzed asymmetric 1,2-alkylsulfonylation of 1,3-dienes

Scheme 17. Photo-induced palladium-catalyzed asymmetric 1,2-carboamination of 1,3-dienes with NHP esters

Scheme 18. Photo-induced palladium-catalyzed asymmetric 1,2-carboamination of 1,3-dienes with bromoamides

Scheme 19. Photo-induced palladium-catalyzed selective cyclization of 1,3-dienes with azabicyclo[1.1.0]butane

Scheme 20. Photo-induced palladium-catalyzed selective alkylacylation of 1,3-dienes

Scheme 21. Photo-induced palladium-catalyzed asymmetric dearomatization of 1,3-dienes with indoles

Scheme 22. Photo-induced palladium-catalyzed 1,4-carbon functionalization of 1,3-dienes

Scheme 23. Photo-induced palladium-catalyzed 1,4-carboamination/cyclization of 1,3-dienes with alkyl halides

Scheme 24. Photo-induced palladium-catalyzed 1,4-carboamination of 1,3-dienes

Scheme 25. Photo-induced palladium-catalyzed carboamination of 1,3-dienes

Scheme 26. Cobalt-catalyzed selective sulfonylarylation of 1,3-dienes

Scheme 27. Cobalt-catalyzed selective 1,2-dicarbofunctionalization of silyl 1,3-dienes

Scheme 28. Cobalt-catalyzed intramolecular cyclization of 1,3-dienes

Scheme 29. Cobalt-catalyzed 3,4-hydroalkylation of 1,3-dienes with aldehydes

Scheme 30. Nickel-catalyzed intramolecular 1,4-carboamination of 1,3-dienes

Scheme 31. Nickel-catalyzed [4＋3] cycloaddition of 1,3-dienes with aziridines

Scheme 32. Nickel-catalyzed 1,4-alkylarylation of 1,3-dienes

Scheme 33. Iron-catalyzed 1,2-dinitrogenation of 1,3-dienes

Scheme 34. Iron-catalyzed 1,2-alkylazidation of 1,3-dienes

Scheme 35. Photo-/copper co-catalyzed asymmetric 1,2-aminocyanation of 1,3-dienes

Scheme 36. Photo-/copper co-catalyzed 1,2-hydroalkoxylation of 1,3-dienes

Scheme 37. Photo-/palladium co-catalyzed asymmetric cyclization/Heck self-coupling of 1,3-dienes

Scheme 38. Photo-/nickel co-catalyzed 1,4-hydroalkylation of 1,3-dienes

Scheme 39. Photo-/nickel co-catalyzed 1,4-sulfonylarylation of 1,3-dienes

Scheme 40. Photo-/cobalt co-catalyzed selective hydrofunctionalization of 1,3-dienes

Scheme 41. Photo-/chromium co-catalyzed asymmetric 1,2-arylalkylation of 1,3-dienes

Scheme 42. Photo-/chromium co-catalyzed asymmetric 1,2-dialkylation of 1,3-dienes

Scheme 43. Photo-/chromium co-catalyzed 1,4-dialkylation of 1,3-dienes

Scheme 44. Photocatalytic 1,4-hydroacylation of 1,3-dienes

Scheme 45. Photocatalytic 1,2-difluoromethyl hydroxylation of 1,3-dienes

Scheme 46. Electrocatalytic 1,2-selenamination of 1,3-dienes

Scheme 47. Electrocatalytic 1,4-alkyletherification of 1,3-dienes

Scheme 48. Electrocatalytic 1,4-dioxygenation of 1,3-dienes with alcohols

Scheme 49. TBAI-catalyzed 1,2-dioxygenation of 1,3-dienes

Scheme 50. Peroxides mediate 1,2-hydroxylated functionalization of 1,3-dienes

Scheme 51. TEMPO disproportionation drives the 1,2-dioxygenation of 1,3-dienes

Scheme 52. Photo-induced brønsted acid-catalyzed 1,2-alkylisothiocyanation of 1,3-dienes

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过渡金属催化自由基介导1,3-二烯的选择性双官能团化研究进展

Recent Advances in Transition Metal-Catalyzed Radical-Mediated Selective Difunctionalization of 1,3-Dienes

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