Copper(I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated N-Heterocycles
| Autor: | Peng Zhang, Christian Wolf, Andrea M. Cook, Yang Liu |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Nucleophilic addition
Molecular Structure 010405 organic chemistry Organic Chemistry chemistry.chemical_element Regioselectivity Bond formation 010402 general chemistry Note 01 natural sciences Copper Amides Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Heterocyclic Compounds Yield (chemistry) Hydrocarbons Chlorinated Organic chemistry Molecule Ethyl chloroformate |
| Zdroj: | The Journal of Organic Chemistry |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon–carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing the corresponding 1,2-dihydro-N-heterocycles in up to 95% yield. |
| Databáze: | OpenAIRE |
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