TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2-<i>a</i>]pyridines with Fluorinated Alcohols
Dhananjay S. Nipate, Sonam Jaspal, Vikki N. Shinde, Krishnan Rangan, Anil Kumar
Abstract
A simple and highly efficient metal-free method has been developed for hydroxyfluoroalkylation of indoles and imidazo[1,2-a]pyridines via TEMPO-mediated C(sp3)–H and C(sp2)–H bond cross-dehydrogenative coupling of fluorinated alcohols and indoles. The protocol showed broad substrate scope, afforded good yields of hydroxyfluoroalkylated products, and was amenable for scale-up. Mechanistic investigation indicated involvement of the radical pathway.
Topics & Concepts
ChemistrySubstrate (aquarium)Combinatorial chemistryCoupling (piping)Scope (computer science)Organic chemistryStereochemistryMedicinal chemistryComputer scienceEngineeringMechanical engineeringOceanographyGeologyProgramming languageCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsFluorine in Organic Chemistry