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Chinese Journal of Organic Chemistry >

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

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

Articles

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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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

Cite this article

Wang Zheng , Yang Liu , Liu Huilan , Bao Wenhu , Tan Yingzhi , Wang Ming , Tang Zilong , He Weimin . Selective Synthesis of Quaternary Carbon Propargylamines from Amines, Alkynes, and Alkynes under Neat Condition[J]. Chinese Journal of Organic Chemistry, 2018 , 38(10) : 2639 -2647 . DOI: 10.6023/cjoc201805033

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