Difluorocarbene-Triggered Acyl Rearrangement Reaction: A Strategy for the Direct Introduction of the <i>gem</i>-Difluoromethylene Group
Haitao Cui, Caijin Ban, Fengting Zhu, Jing‐Mei Yuan, Juan Du, Yanmin Huang, Qi Xiao, Chusheng Huang, Jun Huang, Qiang Zhu
Abstract
A novel metal- and catalyst-free dearomative reaction of 2-oxypyridines to construct gem-difluoromethylenated N-substituted 2-pyridones has been developed. The reaction involves an attractive acyl rearrangement from O to CF2 of difluorocarbene-derived pyridinium ylides, which provides a new strategy for the direct introduction of the gem-difluoromethylene group with high efficiency and selectivity as well as broad substrate scope. Gram-scale synthesis and synthetic transformations have also been demonstrated.
Topics & Concepts
DifluorocarbeneChemistrySubstrate (aquarium)CatalysisCombinatorial chemistryPyridiniumScope (computer science)SelectivityMedicinal chemistryOrganic chemistryComputer scienceGeologyOceanographyProgramming languageFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods