Thiobenzoic Acid-Catalyzed Cα–H Cross Coupling of Benzyl Alcohols with α-Ketoacid Derivatives
Kaichi Sato, Hiromichi Egami, Yoshitaka Hamashima
Abstract
The C-H alkylation of benzyl alcohols with α-ketoacid derivatives was achieved in the presence of thiobenzoic acid with or without Ru or Ir photoredox catalysts. The thiobenzoic acid serves as a photoexcited single-electron reducing reagent and a hydrogen atom transfer catalyst, while addition of the metal photoredox catalyst assists the electron transfer and improves the reaction efficiency. Various functional groups were tolerant of the reaction conditions, and sterically hindered diols were produced in good to high yield.
Topics & Concepts
ChemistryCatalysisYield (engineering)ReagentAlkylationSteric effectsHydrogen atomCombinatorial chemistryCoupling reactionElectron transferPhotochemistryOrganic chemistryMedicinal chemistryAlkylMaterials scienceMetallurgyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques