A General Method for Copper-Catalyzed Arylation of Arene C−H Bonds

A general method for copper-catalyzed arylation of sp2 C−H bonds with pK aʼs below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K3PO4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles suc...

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Bibliographic Details
Published in:	Journal of the American Chemical Society Vol. 130; no. 45; pp. 15185 - 15192
Main Authors:	Do, Hien-Quang, Khan, Rana M. Kashif, Daugulis, Olafs
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 12-11-2008
Subjects:	Benzene Derivatives - chemical synthesis Benzene Derivatives - chemistry Catalysis Copper - chemistry Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry
Online Access:	Get full text
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Summary:	A general method for copper-catalyzed arylation of sp2 C−H bonds with pK aʼs below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K3PO4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper−phenanthroline complex intermediates were independently synthesized.
Bibliography:	Detailed experimental procedures, characterization data for new compounds, and X-ray crystallography data for 2. This material is available free of charge via the Internet at http://pubs.acs.org. ark:/67375/TPS-5WS56F3Z-Z istex:8BAB3CA965BC11F1E30C19F7724E844B5AD194D6 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja805688p