School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, 225002, China.
Org Biomol Chem. 2019 Sep 21;17(35):8175-8184. doi: 10.1039/c9ob01585j. Epub 2019 Aug 29.
A silver-mediated domino radical addition/cyclization reaction of diarylphosphine oxides with propynoic acid derivatives is described in this article. The reaction of diarylphosphine oxides with alkynoates or propynoic amide was regioselective, producing 3-phosphorylated coumarins and benzophosphole oxides in moderate to good isolated yield, respectively. The hydrogen bond between P[double bond, length as m-dash]O and N-H was proposed to assist the vinyl radical regioselective arylation process. The reaction conditions were also compatible with the conversion of dialkylphosphine oxides to 3-phosphorylated-coumarins and quinolin-2(1H)-one in good yields.
本文描述了银介导的二芳基氧化膦与丙炔酸衍生物的多米诺自由基加成/环化反应。二芳基氧化膦与炔酸盐或丙炔酰胺的反应具有区域选择性，分别以中等至良好的分离产率生成 3-膦酰基香豆素和苯并磷杂环氧化物。P[双键，长度 as m-dash]O 与 N-H 之间的氢键被提出有助于协助乙烯基自由基的区域选择性芳基化过程。反应条件也与二烷基氧化膦转化为 3-膦酰基香豆素和喹啉-2(1H)-酮的转化相容，产率良好。
