Photocatalyzed Cascade Hydrogen Atom Transfers for Assembly of Multi‐Substituted α‐SCF3 and α‐SCF2H Cyclopentanones

Abstract

AbstractA photocatalyzed formal (3+2) cycloaddition has been developed to construct original polysubstituted α‐SCF3 cyclopentanones in a regio‐ and diastereoselective manner. This building block approach leverages trifluoromethylthio alkynes and branched/linear aldehydes, as readily available reaction partners, in consecutive hydrogen atom transfers and C−C bond formations. Difluoromethylthio alkynes are also compatible substrates. Furthermore, the potential for telescoped reaction starting from alcohols instead of aldehydes was demonstrated, as well as process automatization and scale‐up under continuous microflow conditions. This prompted density functional theory (DFT) calculations to support a radical‐mediated cascade process.