A facile regiocontrol in the palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodoanilines: a new regioselective synthesis of 2- or 3-fluoroalkylated indole derivatives.
Treatment of various types of fluoroalkylated alkynes with o-iodoaniline in the presence of Pd(PPh(3))(4) in DMF at 80 degrees C for 8 h mainly gave 2-fluoroalkylated indoles in high yields. The use of P(o-Tol)(3) instead of PPh(3) as a ligand led to the preferential formation of 3-fluoroalkylated indoles in high yields. Interestingly, the reaction of trifluoromethylated alkynes bearing a benzylic substituent afforded 2- or 3-trifluoroethylated indole derivatives in good yields.
Konno
Tsutomu
T
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. konno@chem.kit.ac.jp
Chae
Jungha
J
Ishihara
Takashi
T
Yamanaka
Hiroki
H
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005461:Fluorine / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D000814:Aniline Compounds; D007211:Indoles; D005461:Fluorine; D010165:Palladium