American Chemical Society
ol501332g_si_001.pdf (3.4 MB)

Direct Synthesis of Pentafluoroethyl Copper from Pentafluoropropionate as an Economical C2F5 Source: Application to Pentafluoroethylation of Arylboronic Acids and Aryl Bromides

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journal contribution
posted on 2014-07-03, 00:00 authored by Hiroki Serizawa, Kohsuke Aikawa, Koichi Mikami
The direct synthesis of penta­fluoro­ethyl copper (CuC2F5) from a cuprate reagent and ethyl penta­fluoro­propionate as one of the most economical and useful penta­fluoro­ethyl sources was accomplished. The advantages of this method are; all the reagents employed are low-cost and operationally simple, and the CuC2F5 reagent is prepared in virtually quantitative yield. Furthermore, the CuC2F5 reagent prepared was successfully applied to two types of penta­fluoro­ethylations with arylboronic acids and aryl bromides to provide the penta­fluoro­ethylated aromatic products in good-to-excellent yields, including large scale operations.