Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines

doi:10.6023/A23110503

Acta Chimica Sinica ›› 2024, Vol. 82 ›› Issue (2): 190-212.DOI: 10.6023/A23110503 Previous Articles Next Articles

Review

镍催化氮杂环丙烷的开环偶联反应研究

陈健强^a^,^b, 朱钢国^a^,^*(), 吴劼^b^,^c^,^*()

a 浙江师范大学先进催化材料教育部重点实验室浙江金华 321004
b 台州学院医药化工学院&高等研究院浙江台州 318000
c 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032

投稿日期:2023-11-17 发布日期:2023-12-20

作者简介:

陈健强, 博士, 本科毕业于南通大学; 博士毕业于兰州大学(导师: 许鹏飞教授); 2019年11月入职台州学院高等研究院. 主要从事光化学反应研究, 自入职以来以第一作者或通讯作者在Nat. Commun.; Green Chem.; Org. Lett.; Org. Chem. Front.等国际核心期刊上发表论文14篇(其中IF>5.0论文11篇), 授权发明专利3项.

朱钢国, 教授, 博士生导师, 2005年获得中国科学院上海有机化学研究所博士学位, 之后在普渡大学、印第安纳大学相继进行博士后研究, 2008年底回国加入浙江师范大学化学系, 2011年晋升教授, 2020年入选浙江省万人计划科技创新领军人才, 现为浙江师范大学化学与材料科学学院院长, 主要从事有机合成、自由基化学等相关研究. 独立工作以来已在Angew. Chem. Int. Ed.; Nat. Commun.; Chem. Sci.等期刊发表SCI论文80余篇, 授权中国发明专利10多件.

吴劼, 教授、博士生导师. 于2000年6月获得中国科学院上海有机化学研究所博士学位, 之后分别先后在哈佛大学、洛克菲勒大学艾伦•戴蒙德艾滋病研究中心、VivoQuest, Inc. (纽约)从事博士后、访问学者、研究员工作, 2004年回国进入复旦大学化学系担任副教授, 2006年晋升为教授, 博士生导师. 2019年加入台州学院医药化工学院担任院长职务, 主要从事有机合成、药物化学及相关研究工作. 独立工作以来已在Nat. Commun.; J. Am. Chem. Soc.; Angew. Chem. Int. Ed.; Chem. Soc. Rev.等国际核心期刊发表SCI论文360余篇(其中IF>5.0论文220余篇), 论文被引用16500余次(H index 65), 参与编写专著四本, 独立撰写专著一本, 获得美国发明专利2项, 中国发明专利30余项.

基金资助:
国家自然科学基金(22201201); 浙江省自然科学基金(LY23B020001); 浙江省万人计划项目(2020R52021)

Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines

Jianqiang Chen^a^,^b, Gangguo Zhu^a(), Jie Wu^b^,^c()

a Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, Jinhua, Zhejiang 321004
b School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, Taizhou, Zhejiang 318000
c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2023-11-17 Published:2023-12-20
Contact: * E-mail: gangguo@zjnu.cn;jie_wu@fudan.edu.cn
Supported by:
National Natural Science Foundation of China(22201201); Natural Science Foundation of Zhejiang Province(LY23B020001); Zhejiang Provincial Ten Thousand Talent Program(2020R52021)

Aziridines are among the most important building blocks in modern organic synthesis due to their proclivity to ring-opening with a wide range of nucleophiles. This small nitrogen-containing ring system is a highly strained molecule, and C—N fragmentation allows it to be used as the precursor for various scaffolds (including amino alcohols, amino ethers, and diamines) that are not readily accessible through conventional methods. The driving force for this C—N activation is the release of ring strain. In conclusion, significant advances in this filed have been realized with various of nucleophiles. On the other hand, the use of transition metal for C—N activation is one of the most significant methods for the construction of complex molecules. Transition metal-catalyzed ring opening cross-coupling of aziridines have received much attention in recent years. Over the past decades, many groups have described approaches to engage aziridines as electrophiles in nickel-catalyzed cross-coupling. This paper reviews the recent advances in nickel-catalyzed ring opening cross-coupling of aziridines, focuses on the ring-opening methodology, compares the regioselective of the different aziridines, and summarizes generalities of these strategies. We split this paper into three sections consisting of construction of β-functionalized amines via Ni-catalyzed, dual photoredox/Ni-catalyzed, and Ni-catalyzed electrochemical cross-coupling of aziridines. Traditional methods for the ring-opening of aziridines include (1) nickel-catalyzed S_N2 nucleophilic ring-opening, (2) nucleophilic halide ring-opening, and (3) electro-induced ring-opening.

Key words: aziridines, nickel catalysis, photocatalysis, C—N activation, radical

Cite this article

Jianqiang Chen, Gangguo Zhu, Jie Wu. Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines[J]. Acta Chimica Sinica, 2024, 82(2): 190-212.

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Fig. & Tab. 25

Figure 1. Nickel-catalyzed ring opening cross-coupling of aziridines

Figure 2. Oxidative-addition reactions of aziridines with Ni(0)

Figure 3. Carbonylation of azanickellacycles

Figure 4. Ni-catalyzed alkylations of aryl aziridines

Figure 5. Ni-catalyzed functionalization of alkyl aziridines

Figure 6. Ni-catalyzed alkylation of alkyl aziridines

Figure 7. Ni-catalyzed alkylation of disubstituted aziridines

Figure 8. Enantioselective synthesis of azetidines and aziridines

Figure 9. Ni-catalyzed reductive cross-coupling of aziridines with aryl iodides

Figure 10. Ni-catalyzed allylation of aziridines

Figure 11. Ni-catalyzed carboxylation of aziridines

Figure 12. Ni-catalyzed gem-difluoroallylation of aziridines

Figure 13. Ni-catalyzed coupling of aziridines and benzamides

Figure 14. Dual photoredox/Ni-catalyzed alkylation of aziridines

Figure 15. Dual photoredox/Ni-catalyzed arylation of aziridines

Figure 16-1. Dual photoredox/Ni-catalyzed cross-coupling of aziridines with pyridinium salts

Figure 16-2. Mechanism of dual photoredox/Ni-catalyzed cross-coupling of aziridines with pyridinium salts

Figure 17-1. Dual photoredox/Ni-catalyzed acylation of aziridines

Figure 17-2. Mechanism of dual photoredox/Ni-catalyzed acylation of aziridines

Figure 18. Dual photoredox/Ni-catalyzed coupling between aziridines and acetals

Figure 19. Dual photoredox/Ni-catalyzed coupling between aziridines and acetals

Figure 20. Electrochemical reductive cross-coupling of aziridines with aryl iodides

Figure 21. Electrochemical reductive cross-coupling of aziridines with aryl bromides

Figure 22. Ni-catalyzed ring opening arylation of aziridines

Figure 23. Electrochemical reductive cross-coupling of aziridines with alkenyl bromides

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镍催化氮杂环丙烷的开环偶联反应研究

Recent Advances in Nickel-Catalyzed Ring Opening Cross-Coupling of Aziridines

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