Direct Synthesis of Pentafluoroethyl Copper from Pentafluoropropionate
as an Economical C2F5 Source: Application to
Pentafluoroethylation of Arylboronic Acids and Aryl Bromides
posted on 2014-07-03, 00:00authored byHiroki 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.