Related Experiment Video
Updated: Mar 11, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Chemoselective Diazotransfer of Primary Aliphatic Amines into Azides Using Commercial Aryl Sulfonyl Azides
Linlin Xu1, Ningning Song1, Yu Wang1
1State Key Laboratory of Organic-Inorganic Composites, College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, China.
Abstract:
Here, we report that commercial aryl sulfonyl azides efficiently convert primary aliphatic amines into azides under mild conditions. We further show that this diazotransfer reaction exhibits a pronounced preference for aliphatic over aromatic amino groups. This chemoselectivity enables the one-step synthesis of bifunctional molecules bearing both azido and aniline moieties, offering a practical and scalable route to orthogonally "clickable" building blocks for chemical biology and materials modification.
More Related Videos
10:14Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Diazonium Group Substitution: –OH and –H