Copper-Catalyzed Trifluoromethylation of Aryl Iodides with Potassium (Trifluoromethyl)trimethoxyborate

被引:226
作者
Knauber, Thomas [1 ]
Arikan, Fatih [2 ]
Roeschenthaler, Gerd-Volker [2 ]
Goossen, Lukas J. [1 ]
机构
[1] TU Kaiserslautern, Fachbereich Organ Chem, D-67663 Kaiserslautern, Germany
[2] Jacobs Univ Bremen, Sch Sci & Engn, D-28759 Bremen, Germany
关键词
aryl iodide; boron; copper; synthetic methods; trifluoromethylation; CF3; RADICALS; ASYMMETRIC FLUORINATION; REDUCTIVE ELIMINATION; CONVENIENT METHOD; STRATEGIES; CHEMISTRY; PALLADIUM; AGENTS;
D O I
10.1002/chem.201002749
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Potassium (trifluoromethyl)trimethoxyborate is introduced as a new source of CF3 nucleophiles in copper-catalyzed trifluoromethylation reactions. The crystalline salt is stable on storage, easy to handle, and can be obtained in near-quantitative yields simply by mixing B(OMe)(3), CF3SiMe3, and KF. The trifluoromethylation reagent allows the conversion of various aryl iodides into the corresponding benzotrifluorides in high yields under mild, base-free conditions in the presence of catalytic quantities of a Cu-I/1,10-phenanthroline complex.
引用
收藏
页码:2689 / 2697
页数:9
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