自由基介导烯烃的1,2,n-三官能团化反应研究进展

doi:10.6023/cjoc202512033

有机化学 ›› 2026, Vol. 46 ›› Issue (4): 1540-1559.DOI: 10.6023/cjoc202512033 上一篇下一篇

综述与进展

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)

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摘要/Abstract

烯烃作为石油化工领域最具代表性的基础原料之一, 在有机合成等领域中有着不可替代的地位, 与人类社会的发展息息相关. 烯烃分子中碳碳双键的高反应活性为其多样性转化提供了丰富的可能性, 为构建高附加值分子提供了有力的保障. 近年来, 虽然烯烃的1,n-双官能团化研究已取得显著进展, 但在烯烃碳链上实现三官能团化的研究报道较少. 这类反应由于涉及多步电子转移和反应位点竞争以及中间体调控等复杂过程, 对反应选择性控制提出了更高要求, 是本领域前沿研究热点与难点. 可喜的是, 借助自由基的高反应活性和独特成键特性, 已经实现了一些高效的烯烃三官能团化反应. 将系统梳理近年来自由基介导烯烃实现选择性三官能团化领域的研究进展, 重点介绍一些代表性例子并提出展望.

关键词: 烯烃, 三官能团化, 自由基, 光催化

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

引用此文

卢琳玉, 亓雨彤, 张庭珲, 金胜男, 曹中艳, 张洪伟. 自由基介导烯烃的1,2,n-三官能团化反应研究进展[J]. 有机化学, 2026, 46(4): 1540-1559.

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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图/表 22

图式1. 烯烃的双或三官能团化反应

Scheme 1. Di- or trifunctionalization of olefins

图式2. 氰基迁移介导烯烃的三官能团化反应

Scheme 2. Cyano migration-mediated trifunctionalization of alkenes

图式3. 自由基介导氰基迁移的烯烃1,2,n-三官能团化反应

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

图式4. 自由基介导的5-己烯腈1,2,5-三官能团化反应

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

图式5. 氰基迁移和烷基酰化结合实现烯烃的1,2,5-三官能团化

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

图式6. 自由基引发芳基迁移实现α,α-二取代烯丙醇的三官能团化反应

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

图式7. α,α-二取代烯丙醇的1,2, 3-三官能团化反应

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

图式8. 其他自由基引发芳基迁移实现烯烃1,2, 3-三官能团化反应

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

图式9. 三氟甲基或氟烷基自由基引发杂芳基迁移实现烯烃三官能团化反应

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

图式10. 三氟甲基或膦酰基自由基引发杂芳基迁移实现烯烃三官能团化反应

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

图式11. 其他来源的自由基引发杂芳基迁移实现烯烃的三官能团化反应

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

图式12. 硫代磺酸盐/硒磺酸盐参与的杂芳基化烯烃的三官能团化反应

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

图式13. 自由基介导烯烃的甲酰/羰基迁移的三官能团化反应

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

图式14. 自由基引发羰基迁移实现烯烃三官能团化反应

Scheme 14. Free radical induced carbonyl migration to olefins trifunctionalization

图式15. 自由基介导硼基迁移实现烯烃的三官能团化反应

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

图式16. 自由基介导炔基/烯基迁移实现炔丙基醇/烯丙基醇三官能团化反应

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

图式17. 自由基诱导肟基迁移实现烯烃的三官能团化反应

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

图式18. 自由基引导的膦酰基迁移对烯烃的选择性氟烷基化磷酸化反应

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

图式19. 自由基引导氮中心基团迁移实现烯烃的三官能团化反应

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

图式20. 极性[3＋2]环加成与自由基开环过程结合实现非活化烯烃的三官能团化反应

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

图式21. 腙自由基参与的烯烃的三官能团化反应

Scheme 21. Trifunctionalization of alkenes with hydrazone radical participation

图式22. N,N-二氟代磺酰胺作为连续氮自由基前体试剂参与的烯烃三官能团化反应

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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