In this paper, a copper(ii)-catalyzed reaction of o-alkynylanilines with dimethylformamide (DMF) in the presence of oxygen has been developed for synthesizing multisubstituted 3-formyl indole scaffolds.

The utilization of DMF as a dual synthon to serve as a methine source to introduce C2 carbon and nitrogen source to incorporate amino functionality in the 4th position of quinoline under Cu-catalysis.

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In this study, we developed a convenient and efficient two‐step method for the synthesis of ynones in a flow reactor, through the generation of lithium acetylide and its subsequent reactions with acid chlorides. Using this approach, we obtained the ynones in moderate to good yields at room temperature. Moreover, we transformed the ynones into pyrazole derivatives through coupling with hydrazines. This transition metal‐free process, mild reaction conditions, and broad functional group tolerance are all attractive features in comparison with conventional bench‐top methods.