Photocatalyzed Cascade Hydrogen Atom Transfers for Assembly of Multi‐Substituted α‐SCF<sub>3</sub> and α‐SCF<sub>2</sub>H Cyclopentanones
Nicolas Marie, Jun‐An Ma, Vincent Tognetti, Dominique Cahard
Abstract
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.
Topics & Concepts
CascadeConstruct (python library)Hydrogen atomChemistryCycloadditionAtom (system on chip)Combinatorial chemistryStereochemistryComputer scienceCatalysisOrganic chemistryParallel computingProgramming languageChromatographyAlkylFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsRadical Photochemical Reactions