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Br?nsted acid-catalyzed 1,6-hydrophosphination of propargylic para-quinone methides and aza-para-quinone methides for the rapid construction of phosphorus-substituted quaternary carbon centers
Green Synthesis and Catalysis ( IF 8.2 ) Pub Date : 2022-2-1 , DOI: 10.1016/j.gresc.2021.10.005
Ting Xiong , Hao Yuan , Fuxing Yang , Jun Jiang

An intriguing Br?nsted acid-catalyzed 1,6-hydrophosphination of in situ generated propargylic para-quinone methides (p-QMs) and aza-para-quinone methides (aza-p-QMs) with H-phosphorus oxides via dehydration/1,6-addition under ultrasonic irradiation is described. This methodology provides a rapid and green approach for the construction of diarylmethyl phosphorus oxides bearing phosphorus-substituted quaternary carbon centers in high yields (up to 98% yield) within merely 5 ?min. This environmentally benign protocol represents a unique example of 1,6-conjugate additions of propargylic p-QMs and aza-p-QMs for site-selective C–P bond formation in an operationally simple and atom-economical manner. The use of readily available Br?nsted acid catalyst, operationally simplicity, high yields, and high atom economy make this protocol very facile, practical, easily scaled-up and environmentally friendly.

中文翻译:

Br?nsted酸催化炔丙基对醌甲基化物和氮杂对醌甲基化物的1,6-氢膦化用于快速构建磷取代的季碳中心

有趣的 Br?nsted 酸催化 1,6-hydrophosphination 原位生成炔丙基对醌甲基化物 (p-QMs) 和氮杂对醌甲基化物 (aza-p-QMs) 与 H-磷氧化物通过脱水/1描述了超声辐照下的 ,6-加成。该方法为构建带有磷取代季碳中心的二芳基甲基磷氧化物提供了一种快速和绿色的方法,在短短 5 分钟内以高产率(高达 98% 的产率)。这种对环境无害的协议代表了一个独特的例子,即 1,6-共轭添加炔丙基 p-QM 和 aza-p-QM,以操作简单和原子经济的方式进行位点选择性 C-P 键形成。使用现成的 Br?nsted 酸催化剂、操作简单、产率高和原子经济性高,使该协议非常容易、实用、
更新日期:2022-03-28
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