ArticleMolecular diversity2026
Asymmetric C2-functionalization of indoles via visible-light-promoted three-component reaction.
Article in Molecular diversity, 2026. 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
We report a visible-light-driven asymmetric three-component reaction enabling direct enantioselective C2-functionalization of indoles. This method utilizes arylalkynes, benzoquinones, and indoles under chiral phosphoric acid catalysis to construct chiral indole derivatives bearing all-carbon quaternary stereocenters. The reaction proceeds via a cascade sequence: (1) Paternò-Büchi [2 + 2] cycloaddition between arylalkynes and benzoquinones, (2) electrocyclic ring-opening to generate para-quinone methide intermediates, and (3) enantioselective 1,6-addition of indoles at C2 to the para-quinone methide. This single-flask process forges three new bonds with high enantioselectivity. Importantly, exploiting the aldehyde functionality, products are readily transformed into conventionally inaccessible indoles with all-carbon quaternary stereocenters, highlighting the synthetic utility of this methodology.
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