Catalysis Letters

, Volume 142, Issue 5, pp 594–600

Highly Efficient Pd/Tetraphosphine Catalytic System for Copper-Free Sonogashira Reactions of Aryl Bromides with Terminal Alkynes

  • Tao Yi
  • Min Mo
  • Hai-Yan Fu
  • Rui-Xiang Li
  • Hua Chen
  • Xian-Jun Li
Article

DOI: 10.1007/s10562-012-0796-2

Cite this article as:
Yi, T., Mo, M., Fu, H. et al. Catal Lett (2012) 142: 594. doi:10.1007/s10562-012-0796-2

Abstract

In this study, an easily synthesized polydentate ligand N,N,N’,N’-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (1) in combination with [Pd(C3H5)Cl]2 was found to be an active catalyst in copper-free Sonogashira reactions. Most substrates, including steric hindered phenyl bromides and heteroaryl bromides, could couple efficiently with terminal alkynes in the presence of low catalyst loading (0.1 mol%) and this catalytic system showed excellent functional group tolerance. The influence of water in this system was also preliminarily investigated via 31P NMR in situ; that is, appropriate water favors the reaction while excess hindered this reaction.

Graphical Abstract

A simple ligand N,N,N’,N’-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine was employed in Sonogashira reaction with relatively low catalyst loading and isolated yield up to 99 % was obtained in the absence of copper or any other additives. This catalytic system performed high efficiency and excellent functional group tolerance.
https://static-content.springer.com/image/art%3A10.1007%2Fs10562-012-0796-2/MediaObjects/10562_2012_796_Figa_HTML.gif

Keywords

PalladiumTetraphosphineCopper-freeSonogashira reactionAryl bromides

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Tao Yi
    • 1
  • Min Mo
    • 1
  • Hai-Yan Fu
    • 1
  • Rui-Xiang Li
    • 1
  • Hua Chen
    • 1
  • Xian-Jun Li
    • 1
  1. 1.Key Laboratory of Green Chemistry and Technology of the Ministry of Education, College of ChemistrySichuan UniversityChengduPeople’s Republic of China