A class of effective decarboxylative perfluoroalkylating reagents: [(phen)2Cu](O2CRF)

Y. Huang, M.J. Ajitha, K.-W. Huang, Z. Zhang, Z. Weng
Dalton Trans., 45, pp. 8468-8474, (2016)

A class of effective decarboxylative perfluoroalkylating reagents: [(phen)2Cu](O2CRF)

Keywords

Decarboxylative perfluoroalkylating reagents, Aryl and heteroaryl halides

Abstract

This article describes the invention of a class of effective reagents [(phen)2Cu](O2CRF) (1) for the decarboxylative perfluoroalkylation of aryl and heteroaryl halides. Treatment of copper tert-butyloxide with phenanthroline ligands, with subsequent addition of perfluorocarboxylic acids afforded air-stable copper(I) perfluorocarboxylato complexes 1. These complexes reacted with a variety of aryl and heteroaryl halides to form perfluoroalkyl(hetero)arenes in moderate to high yields. Computational studies suggested that the coordination of the second phen ligand may reduce the energy barrier for the decarboxylation of perfluorocarboxylate to facilitate perfluoroalkylation.

Code

DOI: 10.1039/c6dt00277c.

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