Synthesis of Difluorinated Dihydrobenzo[<i>de</i>]chromenes via Rh(III)‐Catalysed C‐H Couplings of 1‐Naphthols with <i>Gem</i>‐Difluoromethylene Alkynes
Liping Li, Xiuhua Zhong, Jiali Xu, Hui Gao, Zhi Zhou, Wei Yi
Abstract
Abstract The Rh(III)‐catalysed C−H couplings of 1‐naphthols with gem ‐difluoromethylene alkynes have been realized for the direct construction of difluorinated dihydrobenzo[ de ]chromenes with broad substrate/functional group compatibility and good regio‐/chemoselectivity and in an atom‐economic manner. The unique fluorine effects account for the unconventional reaction path involving intramolecular 1,3‐hydrogen migration process to afford the exo ‐methylene fragment. magnified image
Topics & Concepts
ChemistryIntramolecular forceChemoselectivityMethyleneHydrogen atomSubstrate (aquarium)Medicinal chemistryStereochemistryCombinatorial chemistryCatalysisComputational chemistryOrganic chemistryAlkylOceanographyGeologyCatalytic C–H Functionalization MethodsFluorine in Organic ChemistrySynthesis and Catalytic Reactions