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Issue 1, 2014
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Copper-catalyzed fluorination of 2-pyridyl aryl bromides

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Abstract

Copper(I)-catalyzed cross-coupling of aryl halides is the subject of extensive interest in synthetic chemistry, but the related catalytic fluorination is unsuccessful. Herein, we have developed a novel copper-catalyzed fluorination of aryl bromides using AgF as the fluorine source. In this transformation a pyridyl directing group is essential for successful catalytic fluorination. A XANES/EXAFS study indicated that the presence of the pyridyl group is essential to stabilize the Cu(I) species and accelerate oxidative addition of the aryl bromide. Further mechanistic studies implicated a Cu(I/III) catalytic cycle in this Cu(I)-catalyzed fluorination, and final aryl C–F bond formation possibly proceeds through an irreversible reductive elimination of the ArCu(III)–F species. This rare report of catalytic fluorination by a copper catalyst provides a valuable foundation for further development of Cu(I)-catalyzed fluorination of aryl halides.

Graphical abstract: Copper-catalyzed fluorination of 2-pyridyl aryl bromides

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Supplementary files

Article information


Submitted
04 Jul 2013
Accepted
27 Sep 2013
First published
27 Sep 2013

Chem. Sci., 2014,5, 275-280
Article type
Edge Article

Copper-catalyzed fluorination of 2-pyridyl aryl bromides

X. Mu, H. Zhang, P. Chen and G. Liu, Chem. Sci., 2014, 5, 275
DOI: 10.1039/C3SC51876K

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