Palladium--phosphinous acid-catalyzed Sonogashira cross-coupling reactions in water.
A palladium--phosphinous acid-catalyzed Sonogashira cross-coupling reaction that proceeds in water under air atmosphere in the absence of organic co-solvents has been developed. Disubstituted alkynes have been prepared in up to 91% yield by POPd-catalyzed coupling of various aryl halides including chlorides in the presence of tetrabutylammonium bromide and pyrrolidine or NaOH.
Wolf
Christian
C
Department of Chemistry, Georgetown University, Washington, DC 20057, USA. cw27@georgetown.edu
Lerebours
Rachel
R
D000388:Air; D000480:Alkynes / Q000737:chemistry; D001272:Atmosphere; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D003429:Cross Reactions; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D009930:Organic Chemicals; D010165:Palladium / Q000737:chemistry*; D017976:Phosphorus Acids / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D012972:Sodium Hydroxide / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D014867:Water / Q000737:chemistry*
D000480:Alkynes; D002712:Chlorides; D006846:Hydrocarbons, Halogenated; D009930:Organic Chemicals; D017976:Phosphorus Acids; D011759:Pyrrolidines; D000644:Quaternary Ammonium Compounds; D012997:Solvents; D014867:Water; D012972:Sodium Hydroxide; D010165:Palladium; C009405:tetrabutylammonium; C032519:pyrrolidine