Copper-catalyzed fluorination of 2-pyridyl aryl bromides

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 transform...

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Bibliographic Details
Published inChemical science (Cambridge) Vol. 5; no. 1; pp. 275 - 280
Main Authors Mu, Xin, Zhang, Hao, Chen, Pinhong, Liu, Guosheng
Format Journal Article
LanguageEnglish
Published 01.01.2014
Subjects
Aromatic compounds
Bonding
Bromides
Catalysis
Catalysts
Fluorination
Halides
Transformations
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Summary: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.
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ISSN:2041-6520
2041-6539
DOI:10.1039/C3SC51876K