Construction of β-Quaternary α,α-Difluoroketones via Catalytic Nucleophilic Substitution of Tertiary Alcohols with Difluoroenoxysilanes
Yong‐Jia Hao, Yi Gong, Ying Zhou, Jian Zhou, Jin‐Sheng Yu
Abstract
An efficient Fe(OTf)3-catalyzed nucleophilic substitution of cyclic or acyclic tertiary alcohols with difluoroenoxysilanes is developed, which provides a facile protocol for assembling structurally diverse α,α-gem-difluoroketones featuring a quaternary carbon center in good to excellent yields under mild conditions. Moreover, the diverse product elaborations highlight the utility of this protocol, as exemplified by the preparation of valuable difluorinated tricyclic indolines.
Topics & Concepts
ChemistryNucleophileNucleophilic substitutionCatalysisQuaternary carbonCombinatorial chemistrySubstitution (logic)Organic chemistryEnantioselective synthesisComputer scienceProgramming languageFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions