Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides
Nickel-Catalyzed Defluorophosphonylation of Aryl Fluorides
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DOI：
10.1021/acs.joc.2c02048
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发表时间：
2022-11-04
影响因子：
3.6
通讯作者：
Sawamura，Masaya
中科院分区：
文献类型：
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作者：
You，Zhensheng;Masuda，Yusuke;Sawamura，Masaya
报道了在叔丁醇钾存在下，镍催化的芳基氟化物与二烷基膦[HP(O)(OR)2](R=仲烷基团)的交叉偶联反应。即使当芳环上存在给电子取代基时，该反应也会将各种芳基氟化物转化为相应的芳基膦酸酯。实验和计算相结合的研究表明，Ni(0)络合物与强给电子型离子桥联二聚亚磷酸盐配体体系[P(OR)2O-K+]2的Ni-K+协同作用促进了芳基氟化物的翻转限制C-F键氧化加成。
A Ni-catalyzed cross-coupling reaction between aryl fluorides and dialkyl phosphonates [HP(O)(OR)2] (R = secondary alkyl groups) in the presence of potassiumtert-butoxide as a base is reported. The reaction converted various aryl fluorides into the corresponding aryl phosphonates even when electron-donating substituents were present on the aromatic ring. The combined experimental and computational studies suggested Ni–K+cooperative action of a Ni(0) complex chelated with a strongly electron-donating ion-bridged dimeric phosphite ligand system [P(OR)2O–K+]2that facilitates turnover-limiting C–F bond oxidative addition of aryl fluorides.