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)
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
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 . DOI: 10.6023/A23110503
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