Nickel-Catalyzed Rearranged Alkenylation of 2‑Arylaziridineswith Aryl Alkenes to Access Allylamines

The transition-metal-catalyzed ring-opening functionalization of aziridines presents a promising approach for synthesizing structurally complex amines. However, the rearranged functionalization of aziridines poses significant challenges. Herein, we report the first rearranged alkenylation of aziridines with aryl alkenes via Ni–Brønsted acid co-catalysis, leading to the rapid synthesis of a diverse array of allylamines with yields reaching up to 91%. Mechanistic studies suggest that the reaction occurs through the rearrangement of aziridine to generate an imine intermediate. This intermediate is subsequently captured by an alkene under nickel catalysis, ultimately leading to the formation of allylamines.

Publication Details

Journal
Figshare
Published
2025-03-10
DOI
https://doi.org/10.1021/acs.orglett.5c00465.s001
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Nickel-Catalyzed Rearranged Alkenylation of 2‑Arylaziridineswith Aryl Alkenes to Access Allylamines

Figshare
Synthesis and Catalytic Reactions
article

Nickel-Catalyzed Rearranged Alkenylation of 2‑Arylaziridineswith Aryl Alkenes to Access Allylamines

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Abstract

The transition-metal-catalyzed ring-opening functionalization of aziridines presents a promising approach for synthesizing structurally complex amines. However, the rearranged functionalization of aziridines poses significant challenges. Herein, we report the first rearranged alkenylation of aziridines with aryl alkenes via Ni–Brønsted acid co-catalysis, leading to the rapid synthesis of a diverse array of allylamines with yields reaching up to 91%. Mechanistic studies suggest that the reaction occurs through the rearrangement of aziridine to generate an imine intermediate. This intermediate is subsequently captured by an alkene under nickel catalysis, ultimately leading to the formation of allylamines.

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Openalex Percentile: Top 51%
Synthesis and Catalytic Reactions
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Nickel-Catalyzed Rearranged Alkenylation of 2‑Arylaziridineswith Aryl Alkenes to Access Allylamines · Figshare (2025) | TGRS Research Map | TGRS