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.
Xu et al. (Mon,) studied this question.