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Water-Promoted Mild and General Michaelis–Arbuzov Reaction of Triaryl Phosphites and Aryl Iodides by Palladium Catalysis
Organic Letters ( IF 5.2 ) Pub Date : 2024-04-11 , DOI: 10.1021/acs.orglett.4c00820
Jin Zhang 1 , Wei Hu 1 , Zihan Chen 1 , Nuo Wu 1 , Chunya Li 1 , Tieqiao Chen 1 , Li-Biao Han 1, 2, 3
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A Pd-catalyzed relatively general Michaelis–Arbuzov reaction of triaryl phosphites and aryl iodides for preparing useful aryl phosphonates was developed. Interestingly, water can greatly facilitate the reaction through a water-participating phosphonium intermediate rearrangement process, which also makes the reaction conditions rather mild. In comparison with the known methods, this reaction is milder and more general, as it exhibits excellent functional group tolerance, can be applied to various triaryl phosphites and aryl iodides, and can be extended to aryl phosphonites and phosphinites. A gram-scale reaction with a low catalyst loading also revealed its practicality and potential in large-scale preparation.

中文翻译:

钯催化水促进亚磷酸三芳基酯和芳基碘化物的温和通用 Michaelis-Arbuzov 反应

开发了一种 Pd 催化的相对通用的亚磷酸三芳基酯和芳基碘化物的 Michaelis-Arbuzov 反应,用于制备有用的芳基膦酸酯。有趣的是,水可以通过水参与的鏻中间体重排过程极大地促进反应,这也使得反应条件相当温和。与已知方法相比,该反应更温和、更通用,具有优异的官能团耐受性,可应用于各种亚磷酸三芳基酯和碘化芳基,并可扩展到亚膦酸芳基酯和次亚膦酸芳基酯。低催化剂负载量的克级反应也揭示了其在大规模制备中的实用性和潜力。
更新日期:2024-04-11
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