C(sp3)—H Bond Oximinylation

doi:10.6023/A25010005

Acta Chimica Sinica ›› 2025, Vol. 83 ›› Issue (4): 390-400.DOI: 10.6023/A25010005 Previous Articles Next Articles

Review

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)

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

Cite this article

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

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Fig. & Tab. 31

Figure 1. Synthetic intermediates generated from oximes and their derivatives

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 16. Photochemical oximinylation of methyl group of alkanes

Scheme 17. NHPI-catalyzed oximinylation of alkanes by TBN

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

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

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

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

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

Scheme 23. Mechanism of photolysis of Barton's nitrite

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

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

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

Scheme 27. Barton reaction of nitrites from chain alcohols

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

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

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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饱和C(sp3)—H键肟化反应