Nickel-Catalyzed Regio- and Enantioselective Hydrofluorination in Unactivated Alkenes

Abstract

While enantioselective hydrofluorination methods for activated alkenes represent a notable advance, the resultant enantiomeric excesses remain largely moderate, indicating the necessity for enhancements in precision, efficiency, and scope. We have recently developed an innovative nickel hydride catalytic system that enables regio- and enantioselective C–F bond formation with unactivated alkenes. By utilizing specially designed Bn-BOx ligands for improved selectivity, our approach demonstrates exceptional efficiency and selectivity with β,γ-alkenyl amide substrates. This breakthrough enhances the synthesis of organofluorine compounds, marking a significant advancement in organic synthesis.

1 Introduction

2 Reaction Design of Hydrofluorination

3 Regio- and Enantioselective Hydrofluorination

4 Asymmetric Amplification

5 Conclusions

Key words

regioselective hydrofluorination - enantioselectivity - nickel hydride catalysis - coordination directing - C(sp³)–F bond formation - unactivated alkene

Publikationsverlauf

Eingereicht: 05. April 2024

Angenommen nach Revision: 28. Mai 2024

Accepted Manuscript online:
28. Mai 2024

Artikel online veröffentlicht:
13. Juni 2024

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