Aziridines as Versatile C(sp3) Precursors in Transition-Metal-Catalyzed Cross-Coupling Strategies

Abstract Aziridines, which serve as valuable scaffolds in numerous pharmaceuticals and bioactive molecules, have emerged as highly efficient C(sp3) precursors in the realm of organic chemistry. Particularly, employing aziridines as versatile electrophiles in transition-metal-catalyzed cross-coupling has enabled precise control over the regiochemistry in the formation of new C(sp3)–C, –Si, and –B bonds. This review explores recent innovative aziridine cross-coupling approaches using Ni or Pd catalysis, highlighting initial findings of new mechanistic approaches and delineating distinct catalytic pathways. 1 Introduction 2 Aziridines Used as C(sp3) Precursors with Organometallic Reagents 2.1 Ni-Catalyzed Aziridine Cross-Coupling 2.2 Pd-Catalyzed Aziridine Cross-Coupling 3 Net-Reductive Approaches via Cross-Electrophile Coupling of Aziridines 3.1 Cross-Electrophile Coupling Using Chemical Reductants 3.2 Electrochemical Reductions in Cross-Electrophile Coupling 4 Aziridine Cross-Coupling via Metallaphotoredox Catalysis 4.1 Net-Reductive Metallaphotoredox-Catalyzed Cross-Coupling 4.2 Redox-Neutral Metallaphotoredox-Catalyzed Cross-Coupling 5 Miscellaneous 6 Conclusion and Future Outlook