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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| Published in | Chemical science (Cambridge) Vol. 5; no. 1; pp. 275 - 280 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
01.01.2014
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| Subjects | |
| Online Access | Get full text |
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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. |
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| AbstractList | 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. |
| Author | Mu, Xin Zhang, Hao Chen, Pinhong Liu, Guosheng |
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| Snippet | Copper(i)-catalyzed cross-coupling of aryl halides is the subject of extensive interest in synthetic chemistry, but the related catalytic fluorination is... |
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| SubjectTerms | Aromatic compounds Bonding Bromides Catalysis Catalysts Fluorination Halides Transformations |
| Title | Copper-catalyzed fluorination of 2-pyridyl aryl bromides |
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