A General Strategy for the Perfluoroalkylation of Arenes and Arylbromides by Using Arylboronate Esters and [(phen)CuRF]

被引:225
作者
Litvinas, Nichole D. [1 ,2 ]
Fier, Patrick S. [1 ,2 ]
Hartwig, John F. [1 ,2 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
关键词
copper; fluorine; one-pot methodology; perfluoroalkylation; trifluoromethylation; COPPER-CATALYZED TRIFLUOROMETHYLATION; ARYL IODIDES; FUNCTIONALIZATION;
D O I
10.1002/anie.201106668
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A versatile method for the synthesis of aryl perfluoroalkanes from arenes and aryl bromides is described. Substituted arenes or aryl bromides are converted in situ to an aryl boronate ester that readily undergoes perfluoroalkylation in air with [(phen)CuR F]. A broad range of aryl bromide substrates were perfluoroalkylated in good yield for the first time. [(phen)CuCF 3] is now commercially available and has been prepared on 20g scale. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:536 / 539
页数:4
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