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Unexpected E-stereoselective reductive A3-coupling reaction of terminal alkynes with aldehydes and amines

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  • Wu Fan

    (Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University)

  • Weiming Yuan

    (Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University)

  • Shengming Ma

    (Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University
    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences)

Abstract

The transition-metal catalysed three-component coupling of an alkyne, an aldehyde and an amine has been became a widely used method for preparing propargylic amines. Here, we report an unexpected copper(I)-catalysed E-stereoselective reduction of propargylic amines in situ formed from readily available terminal alkynes, aldehydes and 3-pyrroline or isoindoline via [1,5]-hydride transfer, affording E-allylic amines. Through mechanistic studies, it is believed that the unsaturated cyclic dialkylamine is acting as hydrogen donor.

Suggested Citation

  • Wu Fan & Weiming Yuan & Shengming Ma, 2014. "Unexpected E-stereoselective reductive A3-coupling reaction of terminal alkynes with aldehydes and amines," Nature Communications, Nature, vol. 5(1), pages 1-9, September.
    • Handle: RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms4884
    DOI: 10.1038/ncomms4884
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    Cited by:

    1. Teng Jia & Yi-Xin Li & Xiao-Hong Ma & Miao-Miao Zhang & Xi-Yan Dong & Jie Ai & Shuang-Quan Zang, 2023. "Atomically precise ultrasmall copper cluster for room-temperature highly regioselective dehydrogenative coupling," Nature Communications, Nature, vol. 14(1), pages 1-15, December.

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