Synthesis of allenamides by copper-catalyzed coupling of allenyl halides with amides, carbamates, and ureas.
[reaction: see text]. A variety of N-substituted allenes have been synthesized by the copper-catalyzed coupling reaction between allenyl halides and amides, carbamates, and ureas. The reactions proceed in good to excellent yield using 7 mol % copper thiophenecarboxylate and 15 mol % of a diamine catalyst.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Stiles
Dylan T
DT
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry*
D000466:Alkadienes; D000577:Amides; D002219:Carbamates; D006846:Hydrocarbons, Halogenated; D003300:Copper; D014508:Urea