Nickel-Catalyzed β-Carboxylation of Ynamides with Carbon Dioxide

Ryohei Doi, Taichi Okano, Iman Abdullah, Yoshihiro Sato

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)


A nickel-catalyzed β-selective hydrocarboxylation of ynamides to give protected dehydro-β-amino acids was developed. The key to exclusive β-selectivity was the use of diethylzinc as a reductant in the presence of a magnesium salt. The reaction was conducted with bis(acetylacetonato)nickel(II) instead of costly and sensitive bis(1,5-cyclooctadiene)nickel(0). In addition, the optimized ligand was inexpensive 1,5-cyclooctadiene. Investigation of the substrate scope revealed that both nitrogen and alkyne substituents have marked effects on the reaction efficiency. We obtained experimental clues that indicated the formation of a vinylzinc intermediate that forms a C-C bond with CO 2 .

Original languageEnglish
Pages (from-to)1048-1052
Number of pages5
Issue number9
Publication statusPublished - 1 Jan 2019


  • carbon dioxide
  • hydrocarboxylation
  • nickel catalysis
  • ynamides
  • β-amino acids


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