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

Hiroki Serizawa, Kohsuke Aikawa and Koichi Mikami*

*Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan, Email: mikami.k.abm.titech.ac.jp

H. Serizawa, K. Aikawa, K. Mikami, Org. Lett., 2014, 16, 3456-3459.

DOI: 10.1021/ol501332g

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Abstract

Pentafluoroethyl copper (CuC₂F₅), which can be synthesized from a cuprate reagent and ethyl pentafluoropropionate in quantitative yield, is an economical and useful pentafluoroethyl source. The reagent was successfully applied to two types of pentafluoroethylations with arylboronic acids and aryl bromides.

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Key Words

perfluoroalkylation

ID: J54-Y2014

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

Hiroki Serizawa, Kohsuke Aikawa and Koichi Mikami*

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