Citation: SHE Chuan, YU Pei, LUO Xingting, TIAN Zaiwen, ZHANG Wanxuan. Synthesis of Alkynyl Selenides by Gold Tribromide Catalyzed Reaction of Terminal Alkynes with Diaryl Diselenides[J]. Chinese Journal of Applied Chemistry, ;2017, 34(10): 1134-1139. doi: 10.11944/j.issn.1000-0518.2017.10.160513 shu

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

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

Corresponding author: ZHANG Wanxuan, zhangwx@hubu.edu.cn
Received Date: 19 December 2016
Revised Date: 13 February 2017
Accepted Date: 29 March 2017

Fund Project: 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)the Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University and Stu-dent Innovation Training Program 201410512002

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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%).
- gold tribromide,
- terminal alkynes,
- diselenides,
- alkynyl selenides
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