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Synfacts 2017; 13(10): 1082
DOI: 10.1055/s-0036-1591277
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Trifluoromethylation of Alkyl Halides

Contributor(s):
Paul Knochel
,
Ferdinand H. Lutter
Shen H. Liu Z. Zhang P. Tan X. Zhang Z. Li C. * Shanghai Institute of Organic Chemistry and Ningbo University of Technology, P. R. of China
Trifluoromethylation of Alkyl Radicals in Aqueous Solution.

J. Am. Chem. Soc. 2017;
139: 9843-9846
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Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Key words

trifluoromethylation - copper - alkyl halides

Significance

The authors developed a copper-mediated trifluoromethylation of various functionalized primary and secondary alkyl bromides and iodides. Using a combination of Et3SiH and K2S2O8 proved to be essential to trigger the radical reaction. The corresponding trifluoromethylated alkyl compounds are obtained in very good yields.


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Comment

Mechanistic experiments were carried out to gain more insight into the mechanism. A radical clock experiment clearly showed the participation of an intermediate alkyl radical. Further studies suggest the involvement of a copper(II) complex as the active species, rather than a copper(III) complex.


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