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2018 , Vol. 38 >Issue 10: 2639 - 2647

DOI: https://doi.org/10.6023/cjoc201805033

研究论文

无溶剂下胺、炔、炔反应选择性构筑季碳炔丙基胺

  • 王峥 ,
  • 杨柳 ,
  • 刘慧兰 ,
  • 谭英芝 ,
  • 包文虎 ,
  • 汪明 ,
  • 唐子龙 ,
  • 何卫民
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  • a 湖南省银杏工程技术研究中心 湖南科技学院 永州 425100;
    b 理论有机化学与功能分子教育部重点实验室 湖南科技大学 湘潭 411201

收稿日期: 2018-05-16

  修回日期: 2018-06-08

  网络出版日期: 2018-06-15

基金资助

国家自然科学基金（Nos.21877034）资助项目.

收起

Selective Synthesis of Quaternary Carbon Propargylamines from Amines, Alkynes, and Alkynes under Neat Condition

  • Wang Zheng ,
  • Yang Liu ,
  • Liu Huilan ,
  • Bao Wenhu ,
  • Tan Yingzhi ,
  • Wang Ming ,
  • Tang Zilong ,
  • He Weimin
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  • a Hunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100;
    b Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201

Received date: 2018-05-16

  Revised date: 2018-06-08

  Online published: 2018-06-15

Supported by

Project supported by the National Natural Science Foundation of China (No. 21877034).

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摘要

在无溶剂下以胺、炔、炔为原料通过“一锅法”串联的反应方便、高效地合成了季碳炔丙基胺.脂肪炔和芳香炔都可以适用于该反应体系.在脂肪炔反应体系中，AgOTf催化促进胺-炔-炔“马氏”反应进程；当芳香炔作为反应底物时，CuBr2/Zn（OTf）2用于共催化剂.该串联反应展示出优异的原子利用效率，为季碳炔丙基胺的制备提供了一种极具有吸引力的绿色合成方法.

关键词： 炔丙基胺; 季碳; 炔; 无溶剂; 绿色有机合成

本文引用格式

王峥 , 杨柳 , 刘慧兰 , 谭英芝 , 包文虎 , 汪明 , 唐子龙 , 何卫民 . 无溶剂下胺、炔、炔反应选择性构筑季碳炔丙基胺[J]. 有机化学, 2018 , 38(10) : 2639 -2647 . DOI: 10.6023/cjoc201805033

Abstract

An efficient and facile method has been developed for the synthesis of quaternary carbon propargylamines via a one-pot tandem reaction of amines, alkynes, and alkynes under neat condition. Both aliphatic and aromatic terminal alkynes are well compatible with the established reaction, with respect to aliphatic alkynes, AgOTf was used as catalyst for the Markovnikov amine-alkyne-alkyne coupling process. When aromatic alkynes were used as substrates, the reaction was promoted by CuBr2/Zn (OTf)2 co-catalytic system. This tandem reaction exhibits excellent atom efficiency and provides an attractive approach to a diverse range of quaternary carbon propargylamines.

Key words： propargylamines; quaternary carbon; alkynes; neat condition; green organic synthesis

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