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Recycling the Waste: The Development of a Catalytic Wittig Reaction

Christopher J. O'Brien *, Jennifer L. Tellez, Zachary S. Nixon, Lauren J. Kang, Andra L. Carter, Stephen R. Kunkel, Katherine C. Przeworski, Gregory A. Chass

*Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Email:

C. J. O'Brien, J. L. Tellez, Z. S. Nixon, L. J. Kang, A. L. Carter, S. R. Kunkel, K. C. Przeworski, G. A. Chass, Angew. Chem. Int. Ed., 2008, 48, 6836-6839.

DOI: 10.1002/anie.200902525

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3-Methyl-1-phenylphospholane-1-oxide as precatalyst and an organosilane reducing agent are the key components in a Wittig reaction catalytic in phosphine. Various heteroaryl, aryl, and alkyl adehydes could be efficiently converted to the corresponding alkenes in good yield using this precatalyst. The protocol also functions well on larger scale.

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proposed catalytic cycle

Key Words

Wittig Reaction, Organocatalysis, Diphenylsilane

ID: J06-Y2009-0750