Trifluoromethylthiolation of Hindered α-Bromoamides with Nucleophilic Trifluoromethylthiolating Reagents
Satoshi Mizuta, Kanami Kitamura, Yuki Morii, Jun Ishihara, Tomoko Yamaguchi, Takeshi Ishikawa
Abstract
General methods have not been previously developed for the synthesis of sterically hindered α-SCF3-substituted carbonyl compounds using nucleophilic trifluoromethylthiolating reagents. Thus, we herein report sp3C–SCF3 bond formation in hindered α-bromoamides containing 3-bromo-oxindoles and linear α-bromoamides using CuSCF3 or AgSCF3 under mild conditions to access sterically hindered α-SCF3-substituted amides. This transformation is applicable to not only 3-SCF3-substituted oxindoles but also primary and secondary amides and reveals a broad functional group tolerance. This method will benefit the fields of medicinal and agricultural chemistry.
Topics & Concepts
ChemistrySteric effectsNucleophileReagentCombinatorial chemistryFunctional groupNucleophilic additionOrganic chemistryCatalysisPolymerFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCarbohydrate Chemistry and Synthesis