Work

Direct catalytic photodecarboxylative amination of carboxylic acids with diazirines: Divergent access to amines, hydrazines, and nitrogen-containing heterocycles

Year: 2024

Type: preprint

Abstract: Amines, hydrazines, and nitrogen-containing heterocycles are pivotal species in medicine, agriculture, fine chemicals, and materials. Diazirines have been recently reported to serve as versatile electrophilic amination reagents for the synthesis of building blocks or late-stage C–N bond formation. Here we report the catalytic photodecarboxylative amination of carboxylic acids with diazirines under mild conditions. The substrate scope includes broad functional group tolerance, such as ketones, esters, olefins, and alcohols, along with the late-stage amination of naproxen, ibuprofen, gemfibrozil, and gibberellic acid. Synthetic applications leverage the versatility of the intermediate diaziridines and include the regioselective preparation of a suite of 1H-indazoles, 2H-indazoles, and fluoroquinolones.

Source: ChemRxiv

DOI: 10.26434/chemrxiv-2024-4vg2s

Authors: Vishala Maharaj, Paresh Athawale, Preeti Chandrachud, Justin Lopchuk

Institutions: University of South Florida, Moffitt Cancer Center

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Moffitt Cancer Center, National Cancer Institute, Division of Chemistry

Awards: G362094, Diazirines and Diaziridines as Nitrogen Transfer Reagents, G4551976579, G8135003176, Moffitt Cancer Center Support Grant