Design and Evolution of Copper Apatite Catalysts for N-Arylation of Heterocycles with Chloro- and Fluoroarenes

We report the preparation of recyclable heterogeneous catalysts, copper-exchanged fluorapatite, and copper-exchanged tert-butoxyapatite by incorporating basic species F-/ t BuO- in apatite in situ by coprecipitation and subsequent exchange with Cu(II). These basic copper catalysts catalyzed N-arylat...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-07, Vol.127 (28), p.9948-9949
Main Authors: Choudary, Boyapati M, Sridhar, Chidara, Kantam, Mannepalli L, Venkanna, Gopaldasu T, Sreedhar, Bojja
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Summary:We report the preparation of recyclable heterogeneous catalysts, copper-exchanged fluorapatite, and copper-exchanged tert-butoxyapatite by incorporating basic species F-/ t BuO- in apatite in situ by coprecipitation and subsequent exchange with Cu(II). These basic copper catalysts catalyzed N-arylation of imidazoles and other heterocycles with chloroarenes and electron-poor fluoroarenes in good to excellent yields. Synthesis and characterization of some of the intermediates of the catalytic cycle gave some insight into the mechanism of the very important organic transformation. The necessity of basic sites for the activation of C−Cl and C−F bonds in the N-arylation of heterocycles with haloarenes is well-established.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja0436594