Issue 43, 2023

Nitrenium ions as new versatile reagents for electrophilic amination

Abstract

Herein we report the utilization of N-heterocyclic nitrenium ions – easily prepared, bench-stable and non-oxidating nitrogen sources for the efficient electrophilic amination of aliphatic and aromatic organometallic nucleophiles, towards the facile and general preparation of primary amines. To this end, a plethora of abundant organolithium and organomagnesium reagents were combined with nitrenium salts to generate a variety of previously unexplored N-alkyl and N-aryl triazanes. Through the simple hydrogenolysis of these relatively stable triazanes, we have prepared a diverse scope of primary amines, including linear and branched aliphatic as well as (hetero)aromatic amines possessing various stereo-electronic substituents. Furthermore, we present the facile synthesis of valuable 15N-labelled primary amines from easily prepared 15N-labelled nitrenium salts, as well as a one-pot approach to biologically relevant primary amines. Finally, a recyclable variant of the nitrenium precursor was prepared and a simple recovery protocol was developed to improve the atom-economy of this procedure.

Graphical abstract: Nitrenium ions as new versatile reagents for electrophilic amination

Supplementary files

Article information

Article type
Edge Article
Submitted
15 ago. 2023
Accepted
25 sep. 2023
First published
30 sep. 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 12034-12040

Nitrenium ions as new versatile reagents for electrophilic amination

I. Avigdori, K. Singh, N. Fridman and M. Gandelman, Chem. Sci., 2023, 14, 12034 DOI: 10.1039/D3SC04268E

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