Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia.
[reaction: see text] Carbonylative coupling of phenylethyne with 4-methoxy-1-iodobenzene in the presence of 1 mol % PdCl(2)(PPh(3))(2), 2 equiv of 0.5 M aqueous ammonia, and CO (1 atm) gives the corresponding alpha,beta-alkynyl ketone in 72% isolated yield after stirring at room temperature for 41 h, while noncarbonylative coupling product is not obtained.
Ahmed
Mohamed S Mohammed
MS
Chemical Resources Laboratory, Tokyo Institute of Technology, 4259 Nagatsuta, Yokohama 226-8503, Japan.
Mori
Atsunori
A
D000480:Alkynes / Q000737:chemistry*; D000641:Ammonia / Q000737:chemistry*; D002384:Catalysis; D007462:Iodobenzenes / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry
D000480:Alkynes; D007462:Iodobenzenes; D007659:Ketones; D009942:Organometallic Compounds; D010165:Palladium; D000641:Ammonia