Heteroarylation of Functionalized Alkenes via Hexafluoroisopropanol-Assisted Redox Activation of Areneazo-2-(2-nitro)propanes.

Authors

Daeun Kim, Soumyadeep Roy Chowdhury, Hun Young Kim, Kyungsoo Oh

Published in

Organic letters. Sep 11, 2026. Epub Sep 11, 2026.

Abstract

The hexafluoroisopropanol (HFIP)-assisted thermal denitrogenative fragmentation of areneazo-2-(2-nitro)propanes enabled heteroarylation of functionalized alkenes through cooperative radical and redox processes. Bench-stable areneazo-2-(2-nitro)propanes served as versatile aryl radical precursors for carboheterocyclization with alkenyl esters, affording diverse arylated lactones and heterocycles with broad functional group tolerance. Mechanistically, the radical fragmentation-nitro-nitrite isomerization of areneazo-2-(2-nitro)propanes generated nitric oxide that underwent a redox process with tertiary radical intermediates to promote heterocyclization. The oxidant-free conditions generated dinitrogen and acetone as benign byproducts.

PMID:
42734495
Bibliographic data and abstract were imported from PubMed on 14 Sep 2026.

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