应用化学2017，Vol.34Issue(10)：1134-1139,6.DOI:10.11944/j.issn.1000-0518.2017.10.160513
三溴化金催化端炔与二芳基二硒醚反应合成炔基硒醚
Synthesis of Alkynyl Selenides by Gold Tribromide Catalyzed Reaction of Terminal Alkynes with Diaryl Diselenides
摘要
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%).关键词
三溴化金/端炔/二芳基二硒醚/炔基硒醚Key words
gold tribromide/terminal alkynes/diselenides/alkynyl selenides分类
化学化工引用本文复制引用
佘川,余佩,骆兴霆,田再文,张万轩..三溴化金催化端炔与二芳基二硒醚反应合成炔基硒醚[J].应用化学,2017,34(10):1134-1139,6.基金项目
湖北大学有机功能分子合成与应用教育部重点实验室和大学生创新训练计划(201410512002)资助项目 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) （201410512002）
