Yang Shiyi, Li Hengzhao, Yu Xiang, An Jie, Szostak Michal
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.
Department of Nutrition and Health, China Agricultural University, Beijing 100193, China.
J Org Chem. 2022 Nov 18;87(22):15250-15260. doi: 10.1021/acs.joc.2c01778. Epub 2022 Oct 28.
A highly efficient protocol for the Suzuki-Miyaura cross-coupling of aryl fluorosulfonates by selective -OF cleavage using well-defined, air- and moisture-stable NHC-Pd(II) chloro dimers is presented. The reaction proceeds in excellent yields and with broad functional group tolerance using 0.10-0.20 mol % of [Pd] in the presence of mild KPO base under aqueous conditions. A variety of sensitive functional groups are tolerated in this operationally trivial protocol for C-O bond activation. Selectivity studies and gram scale cross-coupling are presented. The method advances well-defined and highly reactive Pd(II)-NHCs to the cross-coupling of readily available, orthogonal, and bench-stable fluorosulfonates as aryl halide surrogates.
本文介绍了一种高效的方法，该方法使用定义明确、对空气和湿气稳定的NHC-Pd(II)氯二聚体，通过选择性-OF裂解实现芳基氟磺酸盐的铃木-宫浦交叉偶联反应。在温和的KPO碱存在下，于水相条件下使用0.10-0.20 mol%的[Pd]，该反应能以优异的产率进行，且对官能团具有广泛的耐受性。在这个操作简单的C-O键活化方案中，各种敏感官能团都能被兼容。文中还展示了选择性研究和克级规模的交叉偶联反应。该方法将定义明确且反应活性高的Pd(II)-NHCs应用于作为芳基卤化物替代物的易于获得、正交且稳定的氟磺酸盐的交叉偶联反应中。
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