Palladium-Catalyzed Homocoupling and Cross-Coupling Reactions of Aryl Halides in Poly(ethylene glycol)

The direct coupling of aryl halides to prepare symmetrical and unsymmetrical biaryls were performed successfully in poly(ethylene glycol) (PEG) using Pd(OAc)2 as the catalyst in the absence of other additives or reductants. The selectivity toward biaryl depended on the amount of PEG used. Excessive...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-02, Vol.71 (3), p.1284-1287
Main Authors: Wang, Liang, Zhang, Yuhong, Liu, Leifang, Wang, Yanguang
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Cross-Linking Reagents - chemistry
Exact sciences and technology
Hydrocarbons, Halogenated - chemistry
Iodobenzenes - chemistry
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Palladium - chemistry
Polyethylene Glycols - chemistry
Preparations and properties
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Summary:The direct coupling of aryl halides to prepare symmetrical and unsymmetrical biaryls were performed successfully in poly(ethylene glycol) (PEG) using Pd(OAc)2 as the catalyst in the absence of other additives or reductants. The selectivity toward biaryl depended on the amount of PEG used. Excessive PEGs induce the increase of hydrodehalogenation product, and the best selectivity to biaryl is obtained when the concentration of the hydroxyl group in PEG achieves 100 mol % relative to aryl halides. The catalyst system could be recycled and reused up to five times with no loss of catalytic activity.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo052300a