镍催化氮杂环丙烷的开环偶联反应研究
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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. |
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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. |
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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. |
收稿日期: 2023-11-17
网络出版日期: 2023-12-21
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
Received date: 2023-11-17
Online published: 2023-12-21
Supported by
National Natural Science Foundation of China(22201201); Natural Science Foundation of Zhejiang Province(LY23B020001); Zhejiang Provincial Ten Thousand Talent Program(2020R52021)
氮杂环丙烷类化合物是重要的有机合成子, 其广泛存在于各种有机合成反应当中. 因其独特的三元环结构, 致使其具有较大的环张力. 通常氮杂环丙烷类化合物可以与各种亲核试剂反应, 合成各种传统方法难以合成的β-位取代的胺类化合物, 其中包括氨基醇、氨基醚以及二胺类化合物. 通过亲核试剂开氮杂环丙烷的反应研究已经相当成熟, 此处不再赘述. 此外, 过渡金属催化的C—N活化是一类重要的合成方法. 作为C—N活化重要底物, 过渡金属催化氮杂环丙烷的开环偶联反应取得长足的发展. 尤其是近十年来, 镍催化氮杂环丙烷的开环偶联反应不断涌现. 基于此, 综述了镍催化在氮杂环丙烷开环偶联反应中的研究进展和设计原则, 重点介绍氮杂环丙烷的开环原理, 对比不同取代的氮杂环丙烷区域选择性, 总结不同催化模式下的共性. 本综述将从以下三个方面介绍氮杂环丙烷的开环偶联反应: 其一是单独的镍催化模式; 其二是光/镍协同共催化模式; 其三则是电化学促进的镍催化模式. 对于氮杂环丙烷的开环模式则可以分为: 镍催化的SN2型亲核开环模式、卤素离子亲核开环模式以及电化学还原模式.
陈健强 , 朱钢国 , 吴劼 . 镍催化氮杂环丙烷的开环偶联反应研究[J]. 化学学报, 2024 , 82(2) : 190 -212 . DOI: 10.6023/A23110503
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 SN2 nucleophilic ring-opening, (2) nucleophilic halide ring-opening, and (3) electro-induced ring-opening.
Key words： aziridines; nickel catalysis; photocatalysis; C—N activation; radical
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