ArticleRSC advances2025
Transition metal-free hydrogenative coupling of nitroarenes mediated with dihydropyridine: chemoselective formation of aromatic azoxy, azo, hydrazine and phenazine.
Article in RSC advances, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Due to the diversity of the compounds containing dinitrogen bonds, chemoselectivity is a key issue to be addressed for the hydrogenative coupling of nitroarenes. A system consisting of Hantzsch 1,4-dihydropyridine (HEH) and a base was developed as a transition metal-free reductant for the hydrogenative coupling of nitroarenes to provide aromatic azoxy, azo and hydrazine. Under optimized conditions, the reaction of 2-fluoronitroarene afforded phenazines. Chemoselectivity for the formation of these dinitrogen compounds was effectively regulated by the choice of the base and the amount of reductant employed. A plausible free-radical mechanism for the hydrogenative coupling of nitroarenes was proposed, wherein the combination of HEH and NaH acted as a synergistic reductant.
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