Burton trifluoromethylation

What is Burton trifluoromethylation?

Despite the availability of various methods for incorporating trifluoromethyl groups into aromatic compounds, the Burton trifluoromethylation method, which was first reported in 1985, is considered to be a highly feasible approach for introducing the CF3 group directly into molecules via in situ generation and coupling of CF3Cu with aryl halide.

Burton trifluoromethylation - general reaction scheme
Burton trifluoromethylation

Unlike earlier methods, which had limitations such as the use of expensive reagents or high temperatures, the Burton trifluoromethylation involves the in situ metathesis of (trifluoromethyl)cadmium or (trifluoromethyl)zinc to generate trifluoromethyl copper, which can also be produced from inexpensive difluorodihalomethanes with soluble copper salts. Furthermore, recent developments have shown that CF3Cu is a versatile CF2 transfer reagent capable of forming longer chain CF3(CF2)nCF2-Cu compounds.

References

A remarkably simple preparation of (trifluoromethyl)cadmium and -zinc reagents directly from difluorodihalomethanes
Donald J. Burton and Denise M. Wiemers
Journal of the American Chemical Society 1985 107 (17), 5014-5015
DOI: 10.1021/ja00303a042

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