Organophotoredox-catalyzed deconstructive alkylation/Truce–Smiles rearrangement cascade involving spiro-dihydroquinazolinones and activated alkenes†

Abstract

An organophotoredox-catalyzed cascade reaction involving C–C σ-bond cleavage, C–C bond formation, and a subsequent Truce–Smiles rearrangement has been developed using spiro-dihydroquinazolinones and activated alkenes. This aromaticity-driven deconstructive functionalization strategy efficiently yields valuable quinazolinone-containing long-chain amides bearing an α-all-carbon quaternary center. Mild redox-neutral conditions, good functional group compatibility and high atom economy are the noteworthy features of this methodology.