journal article·2024-08Open access

Direct catalytic photodecarboxylative amination of carboxylic acids with diazirines for divergent access to nitrogen-containing compounds

Vishala Maharaj, Paresh R. Athawale, Preeti P. Chandrachud, Justin M. Lopchuk

Cell Reports Physical Science· Volume 5· Issue 8

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 1 H -indazoles, 2 H -indazoles, and fluoroquinolones.
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Research context

OpenAlex topics: Synthesis and Catalytic Reactions · Catalytic C–H Functionalization Methods · Radical Photochemical Reactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

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