Issue 20, 2016

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
20 Jan 2016
Accepted
13 Apr 2016
First published
13 Apr 2016

Dalton Trans., 2016,45, 8468-8474

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

Y. Huang, M. J. Ajitha, K. Huang, Z. Zhang and Z. Weng, Dalton Trans., 2016, 45, 8468 DOI: 10.1039/C6DT00277C

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