Capture of In Situ Generated Diazo Compounds or Copper Carbenoids by Triphenylphosphine: Selective Synthesis of trans- Alkenes and Unsymmetric Azines via Reaction of Aldehydes with Ketone-Derived N-Tosylhydrazones

Authors

  • Qiang Sha,

    1. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, Fax: +(86)-25-8431-7078
    Search for more papers by this author
  • Yifei Ling,

    1. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, Fax: +(86)-25-8431-7078
    Search for more papers by this author
  • Wenyong Wang,

    1. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, Fax: +(86)-25-8431-7078
    Search for more papers by this author
  • Yunyang Wei

    Corresponding author
    1. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, Fax: +(86)-25-8431-7078
    • School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, Fax: +(86)-25-8431-7078

    Search for more papers by this author

Abstract

Copper(II) acetylacetonate-catalyzed Wittig olefination reactions of aldehydes with ketone-derived N-tosylhydrazones are reported. A series of tosylhydrazones was investigated and our results showed that the carbon number of the alkyl chain influences the E-selecivity of the alkenes greatly. Alkenes could be obtained in moderate yields and excellent E-selectivity when the carbon numbers were up to two. Under metal-free conditions, triphenylphosphine was able to capture the in situ generated diazo compounds and the corresponding unsymmetrical azines were formed in good yields.

original image

Ancillary