Recycling the Waste: The Development of a Catalytic Wittig Reaction

Authors

  • Christopher J. O'Brien Dr.,

    1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Fax: (+1) 817-272-3808
    Search for more papers by this author
  • Jennifer L. Tellez,

    1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Fax: (+1) 817-272-3808
    Search for more papers by this author
  • Zachary S. Nixon,

    1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Fax: (+1) 817-272-3808
    Search for more papers by this author
  • Lauren J. Kang,

    1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Fax: (+1) 817-272-3808
    Search for more papers by this author
  • Andra L. Carter,

    1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Fax: (+1) 817-272-3808
    Search for more papers by this author
  • Stephen R. Kunkel,

    1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Fax: (+1) 817-272-3808
    Search for more papers by this author
  • Katherine C. Przeworski,

    1. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 (USA), Fax: (+1) 817-272-3808
    Search for more papers by this author
  • Gregory A. Chass Dr.

    1. School of Chemistry, University of Wales, Bangor, Wales, LL57 2UW (UK)
    Search for more papers by this author
    • Corresponding author responsible for computational work.


  • We thank The University of Texas at Arlington (UTA) for funding this work and ThalesNano (Hungary) for their collaborative in-kind donation (in part) of an H-Cube Midi used to synthesize 1. C.J.O.B. thanks Prof. Daniel W. Armstrong and Edra Dodbiba for separation of 1. G.A.C. thanks GIOCOMMS for computational resources and CAFMaD (Wales (UK)) for personal support.

Abstract

original image

It's all in the ring: 3-Methyl-1-phenylphospholane-1-oxide (4–10 mol %) and an organosilane reducing agent are the key components in the first Wittig reaction catalytic in phosphine. The protocol also functions well on larger scale: a reaction on a 30 mmol scale yielded 3.39 g of product, corresponding to a yield of 67 %.

Ancillary