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Experimental study demonstrates heteroarylation of functionalized alkenes using areneazo precursors, indicating an efficient, oxidant-free route to diverse arylated lactones.
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.
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Kim et al. (2026) studied this question.
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