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Visible-Light-Induced Cascade Phosphinoylation/Cyclization of Phenacylmalononitriles with Secondary H-phosphine Oxides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-22 , DOI: 10.1002/adsc.202201055
Biquan Xiong 1 , Chonghao Shi 1 , Weifeng Xu 1 , Yu Liu 1 , Longzhi Zhu 1 , Kewen Tang 1 , Shuang-Feng Yin 2 , Wai-Yeung Wong 3
Affiliation  

The visible-light-induced synthesis of 5-phosphoryl-functionalized pyrroles has been established by eosin Y catalysis, and different electron-donating or electron-withdrawing group substituted secondary H-phosphine oxides and phenacylmalononitriles showed good reactivity toward the reaction, affording the cascade phosphinoylation/cyclization products in 82–98% yields via P−C/C−N annulation. Step-by-step control experiments and 31P NMR tracking experiments were further performed to gain the insights of the plausible reaction mechanism and kinetic reaction process. This reaction may have implications for the construction of C(sp2)−P bonds in organophosphorus chemistry.

中文翻译:

可见光诱导的级联膦酰化/苯甲酰基丙二腈与仲 H-氧化膦的环化

已经通过曙红 Y 催化建立了可见光诱导的 5-磷酰基功能化吡咯的合成,不同给电子或吸电子基团取代的仲H-氧化膦和苯甲酰基丙二腈对反应表现出良好的反应性,提供级联反应通过 P−C/C−N 环化,膦酰化/环化产物的产率为 82–98%。进一步进行了逐步控制实验和31 P NMR 跟踪实验,以深入了解似是而非的反应机理和动力学反应过程。该反应可能对有机磷化学中 C( sp 2 )−P 键的构建有影响。
更新日期:2022-11-22
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