4.7 Article

Controlling chemoselectivity in copper-catalyzed decarboxylative A3/A3 cross-couplings: direct formation of unsymmetrical 1,4-diamino-2-butynes

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 4, Issue 1, Pages 37-41

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00499g

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Funding

  1. Natural Science Foundation of Shanghai [15ZR1418800]
  2. Shanghai Municipal Education Commission [ZZGCD15028]
  3. Opening Project of Shanghai Key Laboratory of Chemical Biology, the Shanghai University of Engineering Science [nhrc-2015-15, E1-0501-15-0200]
  4. National Natural Science Foundation of China [21502148]

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A direct cross-coupling of propiolic acid with two kinds of in situ formed iminiums has been achieved via the CuI/CuCl2-catalyzed decarboxylative A(3)/A(3) domino process. This novel protocol to synthesise unsymmetrical 1,4-diamino-2-butynes is operationally simple in an atom-and step-economical manner, and provides products in moderate to excellent yields with high chemoselectivity.

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