A new route to the synthesis of (E)- and (Z)-2-alkene-4-ynoates and nitriles from vic-iiodo-(E)-alkenes catalyzed by Pd(0) nanoparticles in water.
An efficient procedure for the stereoselective synthesis of (E)- and (Z)-2-alkene-4-ynoates and -nitriles by a simple reaction of vic-diiodo-(E)-alkenes with acrylic esters and nitriles catalyzed by in situ prepared Pd(0) nanoparticles in water has been developed. Addition of acrylic esters leads to (E)-isomers exclusively, whereas (Z)-isomers are obtained in high stereoselectivity from reactions of acrylonitrile. The aqueous slurry of Pd nanoparticles is recycled. A probable mechanism has been suggested.
Ranu
Brindaban C
BC
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, India.
Chattopadhyay
Kalicharan
K
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D053758:Nanoparticles / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010316:Particle Size; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000475:Alkenes; D009570:Nitriles; D014867:Water; D010165:Palladium