Oxidative Coupling of Terminal Alkyne with α-Hydroxy Ketone: An Expedient Approach toward Ynediones
作者:Zeguang Zhang、Xuefeng Jiang
DOI:10.1021/ol502298a
日期:2014.9.5
An efficient and mild copper-catalyzed one-pot approach toward ynediones has been established. A variety of ynediones were constructed directly through oxidative coupling of alkyne with alpha-hydroxy ketone. Oxygen-oxidizing and neutral conditions in one-pot for a wide range of substrates including natural product derivatives make this transformation highly efficient and practical. On the basis of control experiments, in situ IR measurements, and isotopic labeling experiments, a plausible mechanism involving intermediate phenylglyoxal was drawn. Applications by synthesis of various heterocycles were also investigated.