Deprotonative Functionalization of the Difluoromethyl Group
Laura L. Santos, Armen Panossian, Morgan Donnard, Jean‐Pierre Vors, Sergii Pazenok, David Bernier, Frédéric R. Leroux
Abstract
The functionalization of 3-(difluoromethyl)pyridine has been developed via direct deprotonation of -CHF 2 with a lithiated base and subsequent trapping with various electrophiles in THF. In situ quenching gives access to 3-pyridyl-CF 2 -SiMe 2 Ph as a new silylated compound, which can be postfunctionalized with a fluoride source to obtain a larger library of 3-(difluoroalkyl)pyridines that could not be accessed via direct deprotonation.
Topics & Concepts
DeprotonationChemistryElectrophileSurface modificationPyridineFluorideTrappingGroup (periodic table)Quenching (fluorescence)Medicinal chemistryCombinatorial chemistryPhotochemistryOrganic chemistryCatalysisInorganic chemistryPhysical chemistryIonEcologyQuantum mechanicsBiologyPhysicsFluorescenceFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsSynthesis and Reactions of Organic Compounds