4.4 Article

Green H2O-Promoted Solvent-Free Synthesis of Enaminocarbonyl Compounds with High Stereoselectivity from Electron-Deficient Terminal Alkynes

Journal

SYNLETT
Volume 31, Issue 9, Pages 878-882

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707968

Keywords

green chemistry; water catalysis; hydroamination; alkynes; enamines

Funding

  1. National Natural Science Foundation of China [21602085, 51902140]
  2. Natural Science Foundation of Jiangsu Province [BK20160551]

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A green H2O-promoted solvent-free hydroamination of electron-deficient terminal alkynes with amines has been developed. All secondary amines, including aliphatic and aromatic amines, gave the corresponding (E)-enamines in good to excellent yields, whereas primary aromatic amines afforded Z-configured products in moderate yields. Propiolates, propyn-1-ones, propynamides, and 1-(ethynylsulfonyl)-4-methylbenzene were explored in this Michael addition.

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