Employing Arylacetylene as a Diene Precursor and Dienophile: Synthesis of Quinoline via the Povarov Reaction

A novel I-2-mediated Povarov reaction of arylacetylenes and anilines for the synthesis of 2,4-substituted quinolines has been developed, in which arylacetylene first acts as both a diene precursor and dienophile. This work further develops the Povarov reaction to expand the types of diene precursors. Preliminary mechanistic studies indicate that the I-2/DMSO system realized the oxidative carbonylation of C(sp)-H of arylacetylene and then undergoes a [4 + 2] cycloaddition reaction.

Automated summary

A novel I-2-mediated Povarov reaction has been developed for the synthesis of 2,4-substituted quinolines using arylacetylenes and anilines. The arylacetylene serves as both a diene precursor and dienophile in this reaction. Preliminary mechanistic studies suggest that the I-2/DMSO system enables the oxidative carbonylation of C(sp)-H of arylacetylene followed by a [4 + 2] cycloaddition reaction.