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

Bruce H. Lipshutz,* Grant T. Aguinaldo, Subir Ghorai and Karl Voigtritter

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

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

DOI: 10.1021/ol800028x (free Supporting Information)


Abstract

Addition of small percentages of the nonionic, vitamin E-based amphiphile “PTS” allows unsymmetrical, E-selective olefin cross-metathesis reactions in water, involving water-insoluble substrates, at room temperature using commercially available catalysts. The nanometer micelles formed accommodate water-insoluble substrates, along with a readily available Ru-based metathesis catalyst.

see article for more examples



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

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

Heck Couplings at Room Temperature in Nanometer Aqueous Micelles

B. H. Lipshutz, B. R. Taft, Org. Lett., 2008, 10, 1329-1332.


Key Words

Cross-Metathesis, Green Chemistry


ID: J54-Y2008-0860