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Rate Enhanced Olefin Cross-Metathesis Reactions: The Copper Iodide Effect

Karl Voigtritter, Subir Ghorai and Bruce H. Lipshutz*

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: lipshutzchem.ucsb.edu

K. Voigtritter, S. Ghorai, B. H. Lipshutz, J. Org. Chem., 2011, 76, 4697-4702.

DOI: 10.1021/jo200360s (free Supporting Information)


Abstract

Copper iodide is an effective cocatalyst for the olefin cross-metathesis reaction. It has both a catalyst stabilizing effect due to iodide ion, as well as copper(I)-based phosphine-scavenging properties. A variety of Michael acceptors and olefinic partners can be cross-coupled under mild conditions in diethyl ether and in water using the new surfactant TPGS-750-M.

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Olefin Cross-Metathesis Reactions at Room Temperature Using the Nonionic Amphiphile “PTS”: Just Add Water

B. H. Lipshutz, G. T. Aquinaldo, S. Ghorai, K. Voigtritter, Org. Lett., 2008, 10, 1325-1328.


Key Words

cross metathesis, α,β-unsaturated carboxylic acid derivatives, green chemistry


ID: J42-Y2011-1710