Department of Organic Chemistry, Indian Institute of Science , Bangalore 560 012, Karnataka, India.
Org Lett. 2015 Oct 2;17(19):4658-61. doi: 10.1021/acs.orglett.5b01810. Epub 2015 Sep 8.
A 1,4-addition with the nucleophilic center generated at the ortho carbon atom of an aromatic ketone in the presence of the highly reactive α-C-H bond, using a directing group strategy, is presented. The reaction yields pharmaceutically useful 3-arylated succinimide derivatives. In order to gain understanding of this redox neutral reaction, despite the presence of copper acetate, and to substantiate the lack of Heck-type products, DFT calculations have been carried out.
本文提出了一种使用导向基团策略,在强反应性的 α-C-H 键存在下,在芳香酮的邻位碳原子上生成亲核中心,从而实现 1,4-加成反应的方法。该反应得到了具有药用价值的 3-芳基琥珀酰亚胺衍生物。为了理解尽管存在醋酸铜但仍为氧化还原中性的反应,并证实没有 Heck 型产物,进行了 DFT 计算。