Work

Room-Temperature Decarboxylative Amination of Electron-Deficient (Hetero)Aromatic Carboxylic Acids

Year: 2026

Type: article

Abstract: Decarboxylative amination reactions offer the opportunity to access (hetero)aromatic amines from readily available carboxylic acid starting materials. However, the reliance of the Curtius rearrangement on organoazides introduces safety concerns, while more recent transition-metal-mediated approaches suffer from high reaction temperatures and limited substrate scopes. Here, we demonstrate a room-temperature decarboxylative amination to generate a wide array of primary (hetero)aromatic amines mediated by N -fluorobenzenesulfonimide (NFSI). The broad functional group tolerance of this reaction enables efficient amination of biologically relevant small molecules. Mechanistic studies suggest that NFSI provides access to an activated sulfonimide intermediate, a functional equivalent to acyl azide intermediates, while avoiding the hazards associated with organoazides.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c05346

Authors: Rabina Basnet, Karl Golian, Jessica Sampson, Jessica M. Hoover

Institutions: University of Minnesota, University of Delaware

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry