Boron Lewis Acid Catalyzed Hydrophosphorylation of N-Heteroaryl-Substituted Alkenes
作者:Sarah Yunmi Lee、Soojin Kwak、Jeongin Choi
DOI:10.1055/a-2218-9298
日期:2024.2
bearing N-heterocycles, including pyridines, a quinoline, a pyrrole, and a benzothiazole, resulting in the production of β-N-heteroaryl alkylphosphonates in good yields under additive-free, operationally simple conditions. The mechanistic insights suggest that this hydrophosphorylation involves the deprotonation of the P–H bond of dialkyl phosphites, enabled by the cooperative effects of a boron acid and
报道了硼路易斯酸催化剂催化的N-杂芳基取代的烯烃的加氢磷酸化。该反应适用于一系列带有N-杂环的烯烃,包括吡啶、喹啉、吡咯和苯并噻唑,从而在无添加剂、操作简单的条件下以良好的收率生产 β- N-杂芳基烷基膦酸酯。机理见解表明,这种加氢磷酸化涉及亚磷酸二烷基酯的 P-H 键的去质子化,这是通过硼酸和烯烃的碱性N-杂环部分的协同作用实现的。所得膦酸根阴离子充当有效的磷亲核试剂,用于与同时形成的N-质子化烯烃进行缀合物加成。这些β- N-杂芳基烷基膦酸酯可以通过引入醇基团或还原氧化膦部分进一步转化为其他有价值的有机磷化合物。