Organic Chemistry Portal

Abstracts

Search:

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: cobrienuta.edu

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 (free Supporting Information)



see article for more reactions

Abstract

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.

see article for more exampels


proposed catalytic cycle



Key Words

Wittig Reaction, Organocatalysis, Silanes


ID: J06-Y2009-0750