Synthesis of heterocyclic allenes via palladium-catalyzed hydride-transfer reaction of propargylic amines.
[reaction: see text] Propargylic diisopropylamines containing heterocycles, which were prepared readily from heterocyclic bromides and propargyldiisopropylamine by the Sonogashira coupling reaction, underwent the allene transformation reaction in the presence of Pd(2)(dba)(3).CHCl(3) catalyst (2.5 mol %) and 1,2-bis[bis(pentafluorophenyl)phosphino]ethane (10 mol %) at 100 degrees C in CHCl(3), giving the corresponding heterocyclic allenes in good to high yields via the palladium-catalyzed hydride-transfer reaction.
Nakamura
Hiroyuki
H
Department of Chemistry, Faculty of Science, Gakushuin University, Mejiro, Toshima-ku, Tokyo 171-8588, Japan. hiroyuki.nakamura@gakushuin.ac.jp
Onagi
Shinya
S
Kamakura
Takaya
T
D000475:Alkenes / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry*; D011437:Propylamines / Q000737:chemistry*
D000475:Alkenes; D006571:Heterocyclic Compounds; D011437:Propylamines; C009054:propargylamine; D010165:Palladium; D006859:Hydrogen; D010293:Pargyline