Copper(I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated <i>N</i>‑Heterocycles

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.本研究以碘化亚铜（copper iodide）为催化剂，在室温条件下实现了炔酰胺（ynamides）与经氯甲酸乙酯（ethyl chloroformate）原位活化的酰氯（acyl chlorides）及氮杂环（N-heterocycles）的加成反应。该经济实用的碳-碳键形成（carbon–carbon bond formation）策略，可从脂肪族与芳香族酰氯出发，便捷合成各类3-氨基炔酮（3-aminoynones），产率最高可达99%。针对吡啶（pyridines）与喹啉（quinolines）的加成反应可在近乎相同的反应条件下进行，且展现出良好至优异的区域选择性（regioselectivity），最终以最高95%的产率得到对应的1,2-二氢氮杂环（1,2-dihydro-N-heterocycles）产物。