Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (10): 1134-1139.DOI: 10.11944/j.issn.1000-0518.2017.10.160513

• Orginal Article • Previous Articles     Next Articles

Synthesis of Alkynyl Selenides by Gold Tribromide Catalyzed Reaction of Terminal Alkynes with Diaryl Diselenides

SHE Chuan,YU Pei,LUO Xingting,TIAN Zaiwen,ZHANG Wanxuan()   

  1. Key Laboratory for the Synthesis and Application of Organic Functional Molecules,Ministry of Education,Hubei Collaborative Innovation Center for Advanced Organic Chemical Material,Hubei University,Wuhan 430062,China
  • Received:2016-12-19 Accepted:2017-03-29 Published:2017-09-29 Online:2017-09-29
  • Contact: ZHANG Wanxuan
  • Supported by:
    Supported by the Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University and Stu-dent Innovation Training Program(No.201410512002)

Abstract:

Alkynyl selenides are important starting materials for the synthesis of some organic selenides. In this paper, alkynyl selenides were synthesized by the reaction between terminal alkynes and diaryl diselenides catalyzed by gold tribromide(AuBr3) in the presence of a base such as potassium carbonate in good to excellent yields(69%~98%). The reaction was performed at 80 ℃ in air, and all the selenium atoms of diaryl diselenides could be taken into use. Dimethyl sulfoxide is a proper solvent. The reaction does not occur when less polar tetrahydrofuran or toluene is used as the solvent. Aryl, alkenyl and alkyl alkynes can smoothly react with diaryl diselenides under the above conditions. Para-substituted phenylacetylene(such as 4-ethynyltoluene, 1-ethynyl-4-methoxybenzene, 4-fluorophenylacetylene, 4-chlorophenylacetylene, etc.) gives rise to alkynyl selenides in good to excellent yields(78%~98%) whether the substituents are electron-donating or -withdrawing. Ortho- and meta-substituted phenylacetylene leads to relatively low yields(69%~82%). Non-aryl alkynes(such as 1-nonyne and 1-ethynylcyclohexene) also afford corresponding alkynyl selenides with high yields(95%).

Key words: gold tribromide, terminal alkynes, diselenides, alkynyl selenides