[Development of novel methods for synthesis of heterocyclic compounds catalyzed by transition metals in fluorinated alcohols].
New possibilities for catalytic syntheses of lactone derivatives and nitrogen-containing heterocyclic compounds in fluorinated alcohols are described. The cationic Rh(I) catalyst in fluorinated alcohol solvents (hexafluoroisopropanol: HFIP, trifluoroethanol: TFE) brought about not only mild cycloaddition reactions of ester-tethered compounds but also a facile formation of indole derivatives by the aromatic amino-Claisen rearrangement of N-propargyl aniline derivatives. The use of HFIP as an additive exerted a remarkable effect on the Pictet-Spengler reaction catalyzed by the fluorinated surfactant-combined Brønsted acid catalyst in water.
Saito
Akio
A
Laboratory of Organic Reaction Chemistry, Showa Pharmaceutical University, Machida City, Japan. akio-sai@ac.shoyaku.ac.jp
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis; D007546:Isoquinolines / Q000138:chemical synthesis; D007783:Lactones / Q000138:chemical synthesis; D008670:Metals; D020005:Propanols; D011725:Pyridines / Q000138:chemical synthesis; D012997:Solvents; D014270:Trifluoroethanol; D006845:Hydrocarbons, Fluorinated
D006571:Heterocyclic Compounds; D007211:Indoles; D007546:Isoquinolines; D007783:Lactones; D008670:Metals; D020005:Propanols; D011725:Pyridines; D012997:Solvents; D014270:Trifluoroethanol; C001337:hexafluoroisopropanol; D006845:Hydrocarbons, Fluorinated; C039109:isoquinoline; C023666:pyridine