Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414006, China.
Org Biomol Chem. 2021 Oct 27;19(41):9012-9020. doi: 10.1039/d1ob01568k.
A nitrogen-centered radical-mediated carbon-carbon bond cleavage strategy is described to synthesize functionalized 3-acylcoumarins. The strategy is enabled by the visible-light-induced acylation/cyclization of alkynoates with various acyl oxime compounds in acetonitrile. The difunctionalization of carbon-carbon triple bonds precedes the generation of iminyl radicals, which is followed by the formation of acyl radicals. The acyl radicals then attack the carbon-carbon triple bonds, followed by 5- cyclization and 1,2-ester migration. This strategy has wide substrate adaptability and good substituent tolerance.
一种氮中心自由基介导的碳-碳键断裂策略被用来合成功能化的 3-酰基香豆素。该策略是通过在乙腈中用光诱导炔酸酯与各种酰基肟化合物的酰化/环化来实现的。碳-碳三键的双官能化先于亚胺基自由基的生成，然后生成酰基自由基。酰基自由基随后攻击碳-碳三键，接着进行 5-环化和 1,2-酯基迁移。该策略具有广泛的底物适应性和良好的取代基容忍性。
