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

Key words

aziridines - cross-coupling - transition-metal catalysis - cross-electrophile coupling - metallaphotoredox reactions - amines

Publication History

Received: 21 July 2024

Accepted after revision: 01 October 2024

Accepted Manuscript online:
06 October 2024

Article published online:
18 November 2024

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