Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Trifluoromethylation of Alkyl Radicals in Aqueous Solution

Trifluoromethylation of Alkyl Radicals in Aqueous Solution
Xinqiang Tan, Pei Zhang, Haigen Shen, Chaozhong Li, Zhonglin Liu, Zhenzhen Zhang
The copper-mediated trifluoromethylation of alkyl radicals is described. The combination of Et3SiH and K2S2O8 initiates the radical reactions of alkyl bromides or iodides with BPyCu(CF3)3 (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)–CF3 intermediates to alkyl radicals is proposed.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06044

DOI: 10.1021/jacs.7b06044

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