Nickel-Catalyzed β-Carboxylation of Ynamides with Carbon Dioxide
| Autor: | Taichi Okano, I. Abdullah, Ryohei Doi, Yoshihiro Sato |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Ligand Organic Chemistry chemistry.chemical_element Substrate (chemistry) Alkyne Diethylzinc 010402 general chemistry 01 natural sciences Nitrogen Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Nickel chemistry Carboxylation |
| Zdroj: | Synlett. 30:1048-1052 |
| ISSN: | 1437-2096 0936-5214 |
| Popis: | 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 CO2. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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