Recent Progress in Radical Mediated 1,2,n-Trifunctiona-lization of Olefins

doi:10.6023/cjoc202512033

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (4): 1540-1559.DOI: 10.6023/cjoc202512033 Previous Articles Next Articles

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自由基介导烯烃的1,2,n-三官能团化反应研究进展

卢琳玉^a, 亓雨彤^a, 张庭珲^b, 金胜男^b, 曹中艳^b^,^*(), 张洪伟^a^,^*()

^a 中国石油大学(华东)化学化工学院山东青岛 266580
^b 河南大学化学与分子科学学院河南开封 450046

收稿日期:2025-12-22 修回日期:2026-02-03 发布日期:2026-02-28
通讯作者: 曹中艳, 张洪伟
基金资助:
山东省自然科学基金(ZR2024MB088); 河南省自然科学基金(252300421183); 河南省自然科学基金(242301420061); 国家自然科学基金(22401077); 中央高校基本科研业务费专项资金(25CX02006A); 河南省高校科技创新人才支持计划(26HASTIT004)

Recent Progress in Radical Mediated 1,2,n-Trifunctiona-lization of Olefins

Linyu Lu^a, Yutong Qi^a, Tinghui Zhang^b, Shengnan Jin^b, Zhongyan Cao^b^,^*(), Hongwei Zhang^a^,^*()

^a College of Chemistry and Chemical Engineering, China University of Petroleum (East China), Qingdao, Shandong 266580
^b College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004

Received:2025-12-22 Revised:2026-02-03 Published:2026-02-28
Contact: Zhongyan Cao, Hongwei Zhang
Supported by:
Natural Science Foundation of Shandong Province(ZR2024MB088); Natural Science Foundation of Henan Province(252300421183); Natural Science Foundation of Henan Province(242301420061); National Natural Science Foundation of China(22401077); Fundamental Research Funds for the Central Universities(25CX02006A); Program for Science & Technology Innovation Talents in Universities of Henan Province(26HASTIT004)

Olefins, as representative fundamental feedstocks in the petrochemical industry, occupy an irreplaceable position in organic synthesis, and are closely linked to the progress of modern society. The high reactivity of the carbon-carbon double bond endows olefins with remarkable versatility in chemical transformations, thereby providing a powerful platform for building highly-valued molecule. In recent years, although significant progress has been made in olefin difunctionalization, the development of methods for introducing three distinct functional groups into a single olefin molecule remains underexplored. Such transformations are inherently more challenging, as they involve complex processes such as multistep electron transfer, competition among reactive sites, and fine control over intermediate species, which has emerged as a frontier area in modern organic synthesis. Delightly, some excellent examples that enable to achieve the trifunctionalization of alkenes by borrowing the high reactivity and unique bond construction properties of radicals, have been disclosed recently. This review provides a systematic summary of recent advances in radical-mediated trifunctionalization of olefins, with a particular focus on repre- sentative examples, and offers perspectives on future opportunities and challenges in this rapidly evolving field.

Key words: olefin, trifunctionalization, radical, photocatalysis

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Linyu Lu, Yutong Qi, Tinghui Zhang, Shengnan Jin, Zhongyan Cao, Hongwei Zhang. Recent Progress in Radical Mediated 1,2,n-Trifunctiona-lization of Olefins[J]. Chinese Journal of Organic Chemistry, 2026, 46(4): 1540-1559.

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Fig. & Tab. 22

Scheme 1. Di- or trifunctionalization of olefins

Scheme 2. Cyano migration-mediated trifunctionalization of alkenes

Scheme 3. 1,2,n-Trifunctionalizationof olefins mediated by free radical cyanide migration

Scheme 4. Free radical mediated 1,2,5-trifunctionalization of 5-hexenenitrile

Scheme 5. Combining cyano migration and alkyl acylation to 1,2,5-trifunctionalization of olefin

Scheme 6. Radical-initiated aryl migration for the trifunctionalization of α,α-disubstituted allylic alcohols

Scheme 7. 1,2,3-Trifunctionalization of α,α-disubstituted allylic alcohols

Scheme 8. Other free radicals trigger aryl migration to 1,2, 3-trigunctionalization of olefins

Scheme 9. Trifluoromethyl or fluoroalkyl radicals induce heteroaryl migration to achieve alkene trifunctionalization

Scheme 10. Trifluoromethyl or phosphonyl radicals initiate heteroaryl migration to achieve alkene trifunctionalization

Scheme 11. Free radicals from other sources initiate heteroaryl migration to achieve the trifunctionalization of alkenes

Scheme 12. Trifunctionalization of heteroaryl-substituted alkenes involving thiosulfonates/seleninosulfonates

Scheme 13. Trifunctionalization of formyl/carbonyl migration of olefins mediated by free radicals

Scheme 14. Free radical induced carbonyl migration to olefins trifunctionalization

Scheme 15. Free radical mediated boron migration for trifunctionalization of olefins

Scheme 16. Free radical mediated migration of alkynyl/allyl groups for the functionalization of propargyl/allyl alcohols

Scheme 17. Free radical induced migration of oxime groups for trifunctionalization of olefins

Scheme 18. Radical-guided phosphinyl migration for selective fluoroalkyl phosphorylation of alkene

Scheme 19. Radical-guided nitrogen-centered group migration enables the trifunctionalization of alkenes

Scheme 20. Combining polar [3＋2] cycloaddition with radical ring opening process totrifunctionalization of unactivated olefins

Scheme 21. Trifunctionalization of alkenes with hydrazone radical participation

Scheme 22. N,N-Difluorosulfonamide as a continuous nitrogen radical precursor reagent for olefin trifunctionalization

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自由基介导烯烃的1,2,n-三官能团化反应研究进展

Recent Progress in Radical Mediated 1,2,n-Trifunctiona-lization of Olefins

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