A New Route to the Synthesis of (E)- and (Z)-2-Alkene-4-ynoates and Nitriles from vic-Diiodo-(E)-alkenes Catalyzed by Pd(0) Nanoparticles in Water
Brindaban C. Ranu* and Kalicharan Chattopadhyay
*Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India, Email: ocbcriacs.res.in
B. C. Ranu, K. Chattopadhyay, Org. Lett., 2007, 9, 2409-2412.
DOI: 10.1021/ol0708121 (free Supporting Information)
An efficient, palladium-catalyzed synthesis of 2-alkene-4-ynoates and -nitriles by a simple reaction of vic-diiodo-(E)-alkenes with acrylic esters and nitriles in water leads to (E)-isomers from acrylic esters exclusively, whereas (Z)-isomers are obtained in high stereoselectivity from reactions of acrylonitrile. The in situ prepared Pd(0) nanoparticles can be recycled.
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B. C. Ranu, L. Adak, K. Chattopadhyay, J. Org. Chem., 2008, 73, 5609-5612.