铜介导的不饱和钾有机三氟硼酸盐的自由基三氟甲基化反应。
Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates.
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
出版信息
J Org Chem. 2013 Dec 20;78(24):12837-43. doi: 10.1021/jo4023233. Epub 2013 Nov 19.
Abstract
Copper-mediated trifluoromethylation of unsaturated organotrifluoroborates with the Langlois reagent (NaSO2CF3) and TBHP allows the introduction of trifluoromethyl groups into a variety of organic substructures. The reactions are easy to set up, the conditions are mild and general, and the process provides access to trifluoromethylated alkynes, alkenes, arenes, and heteroarenes in fair to good yields.
摘要
铜介导的不饱和三氟硼酸盐与 Langlois 试剂（NaSO2CF3）和 TBHP 的三氟甲基化反应，可将三氟甲基基团引入各种有机结构中。这些反应易于进行，条件温和且通用，该过程可在中等至良好的收率下得到三氟甲基化的炔烃、烯烃、芳烃和杂芳烃。
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2
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