三氟甲基化的烷基自由基在水溶液中。
Trifluoromethylation of Alkyl Radicals in Aqueous Solution.
机构信息
Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
School of Materials and Chemical Engineering, Ningbo University of Technology , No. 201 Fenghua Road, Ningbo 315211, P. R. China.
出版信息
J Am Chem Soc. 2017 Jul 26;139(29):9843-9846. doi: 10.1021/jacs.7b06044. Epub 2017 Jul 12.
The copper-mediated trifluoromethylation of alkyl radicals is described. The combination of EtSiH and KSO initiates the radical reactions of alkyl bromides or iodides with BPyCu(CF) (BPy = 2,2'-bipyridine) in aqueous acetone at room temperature to afford the corresponding trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl halides and exhibits wide functional group compatibility. A mechanism involving trifluoromethyl group transfer from Cu(II)-CF intermediates to alkyl radicals is proposed.
本文描述了铜介导的自由基三氟甲基化反应。在室温下，EtSiH 和 KSO 的组合引发了烷基溴化物或碘化物与 BPyCu(CF)（BPy = 2,2'-联吡啶）在水/丙酮中的自由基反应，以高产率得到相应的三氟甲基化产物。该方案适用于各种伯烷基和仲烷基卤化物，并表现出广泛的官能团兼容性。提出了一种涉及 Cu(II)-CF 中间体向自由基转移三氟甲基的反应机制。
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