饱和C(sp3)—H键肟化反应

doi:10.6023/A25010005

化学学报 ›› 2025, Vol. 83 ›› Issue (4): 390-400.DOI: 10.6023/A25010005 上一篇下一篇

综述

饱和C(sp³)—H键肟化反应

徐安佗^a^,^b, 李骏一^a, 刘强^a^,^*()

a 兰州大学天然产物化学全国重点实验室兰州 730000
b 南通诺泰生物医药技术有限公司南通 226133

投稿日期:2025-01-02 发布日期:2025-03-12

作者简介:

徐安佗, 2001年毕业于兰州大学化学系, 获得学士学位, 自2002年起, 一直在制药行业从事药物化学研发和管理工作. 目前经营一家医药研发公司.

李骏一, 2024年毕业于兰州大学, 获学士学位. 目前在兰州大学攻读硕士学位. 研究兴趣为N-亚硝胺类化合物键均裂反应.

刘强, 2001年和2006年分别在兰州大学获得学士和博士学位. 2009年~至今, 历任兰州大学讲师、副教授、教授. 2009年~2011年, 中国科学院理化技术研究所超分子光化学研究组从事博士后研究. 现为兰州大学天然产物化学全国重点实验室教授, 博士生导师, 中国化学会光化学专业委员会委员. 主要研究领域涉及有机光化学和自由基合成化学.

† 共同第一作者.

基金资助:
甘肃省科技重大专项(22ZD6FA006); 及国家自然科学基金(21871123); 及国家自然科学基金(22171120)

C(sp³)—H Bond Oximinylation

Antuo Xu^a^,^b, Junyi Li^a, Qiang Liu^a()

a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000
b Nantong Noatic Bio-Pharm Technology Co., Ltd., Nantong 226133

Received:2025-01-02 Published:2025-03-12
Contact: * E-mail: liuqiang@lzu.edu.cn
About author:† These authors contributed equally to this work.
Supported by:
Science and Technology Major Program of Gansu Province of China(22ZD6FA006); National Natural Science Foundation of China(21871123); National Natural Science Foundation of China(22171120)

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摘要/Abstract

肟是一种常见有机化合物, 在化学、生物、环境、医药、农药、材料等领域及相关的工业生产中具有多种用途. 在众多合成方法中, 将烃类化合物碳氢键直接转化为肟官能团无疑是合成肟最直接和有效的手段. 活性亚甲基和甲基C(sp³)—H键的肟化反应通常依赖于亚硝酸、亚硝酰氯、亚硝酸盐和亚硝酰酯等肟化试剂, 其中亚硝酰阳离子(NO⁺)作为关键中间体参与反应. 相比之下, 自由基介导的肟化反应展现出更广泛的底物适用性, 甚至能够作用于仅含有未活化C(sp³)—H键的底物. 从反应机理来看, 该过程通常通过光照或加热引发亚硝基化合物的均裂, 生成一个以杂原子为中心的自由基和一氧化氮. 随后, 以杂原子为中心的自由基从底物中攫取一个氢原子, 形成烷基自由基. 该烷基自由基进一步参与后续的自由基反应, 并最终与一氧化氮发生偶联. 这种偶联反应生成亚硝基中间体, 随后通过异构化转化为目标肟产物. 梳理了从20世纪初至今饱和C(sp³)—H键的肟化反应, 按照反应历程不同, 分别对活泼亚甲基及甲基C(sp³)—H肟化反应、自由基介导的饱和C(sp³)—H键的肟化反应及金属介导的饱和C(sp³)—H键的肟化反应进行了综述, 并对该领域的局限性和未来发展方向做出了简要分析.

关键词: C—H键活化, 肟, 肟化反应, 一氧化氮, 亚硝酰正离子

Oxime is a widely used organic compound with numerous applications in chemistry, biology, environmental science, medicine, pesticides, materials, and related industrial production. Among the various synthetic methods, directly converting carbon-hydrogen bonds in hydrocarbon compounds into oximes is the most straightforward and practical approach for synthesizing oximes. The oximinylations of reactive methylene and methyl C(sp³)—H bonds often involve oximinylating reagents such as nitrous acid, nitrosyl halides, nitrite, and nitrosyl esters, with the nitrosyl cation as a crucial intermediate. In contrast, radical-mediated oximinylations have a broader substrate scope and can even be applied to substrates containing only unactivated C(sp³)—H bonds. Mechanistically, the reactions involve the homolytic cleavage of a nitroso compound via light irradiation or heating, generating a heteroatom-centered radical and a nitric oxide radical. The heteroatom-centered radical subsequently abstracts a hydrogen atom from the substrate to form an alkyl radical, which then undergoes subsequent radical reactions and finally couples with the nitric oxide radical. This coupling produces a nitroso intermediate, which isomerizes to oxime. This paper reviews the oximinylations of saturated C(sp³)—H bonds from the early 20th century to the present. It categorizes the reactions based on their mechanisms, including the oximinylations of reactive methylene and methyl C(sp³)—H bonds, radical-mediated oximinylations of C(sp³)—H bonds, and metal-mediated oximinylations of C(sp³)—H bonds. Additionally, this paper not only elucidates the development of the C(sp³)—H oximinylation reaction but also discusses the challenges in this field and offers future perspectives with the aim of providing insights for innovative applications in synthetic chemistry and industrial processes.

Key words: C—H bond activation, oxime, oximinylation, nitric oxide, nitrosyl cation

引用此文

徐安佗, 李骏一, 刘强. 饱和C(sp³)—H键肟化反应[J]. 化学学报, 2025, 83(4): 390-400.

Antuo Xu, Junyi Li, Qiang Liu. C(sp³)—H Bond Oximinylation[J]. Acta Chimica Sinica, 2025, 83(4): 390-400.

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图/表 31

图1. 肟及其衍生物生成的部分合成中间体

Figure 1. Synthetic intermediates generated from oximes and their derivatives

图式1. 亚硝酸酯类化合物对活泼亚甲基的C(sp3)—H肟化反应

Scheme 1. C(sp3)—H oximinylation of active methylene groups by nitrites

图式2. 亚硝酸酯对脂肪酮类化合物α-CH2肟化反应

Scheme 2. Oximinylation of α-CH2 of aliphatic ketones by nitrites

图式3. 亚硝酸酯对芳香酮类化合物α-CH2肟化反应

Scheme 3. Oximinylation of α-CH2 of aromatic ketones by nitrites

图式4. NOCl对中环酮类化合物α-CH2的肟化反应

Scheme 4. Oximinylation of the mesocyclic ketone α-CH2 by NOCl

图式5. 1,3-二羰基化合物α-CH2的肟化反应

Scheme 5. Oximinylation of α-CH2 of 1,3-dicarbonyl compounds

图式6. 羰基化合物α-CH2肟化反应历程

Scheme 6. Mechanism of oximinylation of α-CH2 of carbonyl compounds

图式7. BF3催化螺缩酮α-C(sp3)—H键肟化

Scheme 7. BF3-catalysis oximinylation of spirochromone α-C(sp3)—H

图式8. 布朗斯特酸催化TBN对2-烷基氮杂芳烃C(sp3)—H键肟化

Scheme 8. C(sp3)—H oximinylation of 2-alkylazaroles via Br?nsted acid-catalyzed nucleophilic addition to TBN

图式9. 碱性下TBN对双苄位C(sp3)—H键肟化

Scheme 9. Oximinylation of dibenzyl C(sp3)—H by TBN under alkaline

图式10. 自由基介导饱和C(sp3)—H键肟化反应的一般机理

Scheme 10. General mechanism of radical-mediated oximinylation of saturated C(sp3)—H bonds

图式11. NOCl肟化烷烃C(sp3)—H键

Scheme 11. Oximinylation of alkane C(sp3)—H bond by NOCl under sunlight

图式12. NOCl对甲苯C(sp3)—H键的肟化

Scheme 12. Oximinylation of C(sp3)—H bond in toluene by NOCl

图式13. 光驱动NOCl肟化反应的自由基历程

Scheme 13. Radical process of light-driven oximinylation using NOCl

图式14. 氯气与一氧化氮对C(sp3)—H肟化及亚硝化

Scheme 14. Oximinylation and nitrosation of C(sp3)—H bond by chlorine and nitric oxide

图式15. 自由基介导光催化TBN实现对饱和C(sp3)—H的肟化

Scheme 15. Radical mediated photocatalytic oximinylation of C(sp3)—H using TBN

图式16. 光驱动烷烃甲基肟化反应

Scheme 16. Photochemical oximinylation of methyl group of alkanes

图式17. NHPI催化TBN对烷烃C(sp3)—H的肟化反应

Scheme 17. NHPI-catalyzed oximinylation of alkanes by TBN

图式18. 一锅法反应实现环十二烷肟化并重排生成月桂内酰胺

Scheme 18. One-pot reaction for the oximinylation and rearrangement of cyclododecane to form laurolactam

图式19. TBN和水相中由2-吲哚酮制备靛红-3-肟

Scheme 19. Synthesis of isatin oximes from oxindoles and TBN in water

图式20. 可见光催化TBN对环己烷肟化反应

Scheme 20. Visible light-catalyzed oximinylation of cyclohexane by TBN

图式21. 利用流动化学实现NaNO2与HCl对环己烷肟化反应

Scheme 21. Flow chemical oximinylation of cyclohexane using NaNO2 and HCl

图式22. 流动反应-加热蒸馏串联选择性肟化烃类C(sp3)—H键

Scheme 22. Selective oximinylation of C(sp3)—H bond using TBN by flow reaction-distillation tandem

图式23. 巴顿亚硝酸酯光解肟化反应历程

Scheme 23. Mechanism of photolysis of Barton's nitrite

图式24. 巴顿反应在甾体化合物远程官能团化中的应用

Scheme 24. Application of the photolysis of Barton's nitrite to the remote functionalization of steroidal compounds

图式25. 巴顿反应中C(sp3)—H肟化位点的选择性

Scheme 25. Site-selectivity of C(sp3)—H oximinylation in the photolysis of Barton's nitrite

图式26. 巴顿反应在全氢组氨酸毒素合成中的应用

Scheme 26. Application of Barton's nitrite photolysis in the synthesis of perhydrohistrionicotoxin

图式27. 链状醇对应的亚硝酸酯发生巴顿反应

Scheme 27. Barton reaction of nitrites from chain alcohols

图式28. 可见光催化N-亚硝酰胺为原料生成苯并[1,2]噁嗪-1-酮

Scheme 28. Visible light-catalyzed generation of benzo[1,2]oxazin-1- one from N-nitrosamides

图式29. NiCl2?6H2O与α-CH2肟生成邻二肟配合物

Scheme 29. NiCl2?6H2O and α-CH2 oxime to form o-dioxime complexes

图式30. Cu(OAc)2/NHPI催化甲苯类化合物肟化

Scheme 30. Cu(OAc)2/NHPI-catalyzed oximinylation of toluene analogs

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饱和C(sp³)—H键肟化反应

C(sp³)—H Bond Oximinylation

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