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N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines
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N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines
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Journal Article
N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines
2022
Overview
N-
functionalized aziridines, which are both useful intermediates and important synthetic targets, can be envisioned as arising from the addition of nitrenes (
i.e
., NR fragments) to olefinic substrates. The exceptional reactivity of most nitrenes, in particular with respect to unimolecular decomposition, prevents general application of nitrene-transfer to the synthesis of
N
-functionalized aziridines. Here we demonstrate
N
-aryl aziridine synthesis via 1) olefin aziridination with
N
-aminopyridinium reagents to afford
N
-pyridinium aziridines followed by 2) Ni-catalyzed C–N cross-coupling of the
N
-pyridinium aziridines with aryl boronic acids. The
N
-pyridinium aziridine intermediates also participate in ring-opening chemistry with a variety of nucleophiles to afford 1,2-aminofunctionalization products. Mechanistic investigations indicate aziridine cross-coupling proceeds via a noncanonical mechanism involving initial aziridine opening promoted by the bromide counterion of the Ni catalyst, C–N cross-coupling, and finally aziridine reclosure. Together, these results provide new opportunities to achieve selective incorporation of generic aryl nitrene equivalents in organic molecules.
Aziridines are useful intermediates, present in important synthetic targets. Here, the authors show a strategy for the synthesis of N-aryl aziridines based on N-aminopyridinium reagents followed by Ni-catalyzed C–N cross-coupling of N-pyridinium aziridines with aryl boronic acids.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
