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DOI: 10.1055/s-0029-1218105
Catalytic Wittig Reaction via in situ Phosphine Oxide Recycling
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*
University of Texas at Arlington, USA and University of Wales, Bangor, UK
Publication History
Publication Date:
22 October 2009 (online)
Significance
A phosphine-catalyzed Wittig-type reaction is reported. Several aromatic and aliphatic aldehydes react with various halides in good to high yields and diastereoselectivity. Even a trisubstituted alkene can be formed in high yield and with reasonable E/Z control. In the proposed catalytic cycle phosphine oxide precatalyst 1 is reduced by organosilane 2 to the corresponding active phosphine catalyst 3, which reacts with the alkyl halide to the ylide, undergoing a Wittig reaction. Computational studies support the suggestion that 1 is more easily reduced than triphenylphosphine oxide; therefore, the use of catalyst 1 is necessary.
Review: F. E. Kühn, A. M. Santos Mini-Rev. Org. Chem. 2004, 1, 55-64.