Solid-phase organic synthesis of difluoroalkyl entities using a novel fluorinating cleavage strategy: part 2. Synthesis of three small gem-difluorinated compound libraries using a dithiane linker.
Three small compound biaryl libraries featuring a novel fluorinating cleavage strategy for preparation of a difluoromethyl group were assembled on solid supports. The average reaction yield per step was up to 96% in a synthetic sequence over five to six steps. Key features were Suzuki coupling reactions, transesterification with potassium cyanide and amidation reaction with trimethyl aluminum on solid supports.
Wiehn
Matthias S
MS
Institut fur Organische Chemie, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.
Fürniss
Daniel
D
Bräse
Stefan
S
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry*; D054852:Small Molecule Libraries; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
D006845:Hydrocarbons, Fluorinated; D011807:Quinolizines; D054852:Small Molecule Libraries; D013457:Sulfur Compounds; C438055:dithiane