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Open air O-arylation reaction of phenols with aryl halides catalyzed by polymer-anchored copper(II) complexes

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Abstract

Two copper complexes were synthesized from macroporous chloromethylated polystyrene beads. The first one was prepared by sequential attachment of imidazole and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer, and the second one was prepared from 4-vinylpyridine and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer. These catalysts showed excellent catalytic activity in O-arylation reaction of aryl halides with phenol in dimethylsulfoxide using potassium carbonate at 130 °C under open air conditions to give diaryl ethers in high yields. Less reactive aryl bromides and aryl chlorides have also been shown to react with phenols to give good yields of the diaryl ethers. The effects of various parameters such as solvent, catalyst from different copper salt and base on the reaction system were studied. The reaction is applicable to a wide variety of substituted aryl halides and phenols with different steric and electronic properties. These catalysts were recovered by simple filtration, and the reusability experiments showed that these catalysts can be used five times without much loss in the catalytic activity.

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Acknowledgments

We thank the Department of chemistry, University of Calcutta, for providing us the instrumental support. We gratefully acknowledge DST, New Delhi, for award of grant under its FIST program to the Department of Chemistry, University of Kalyani. SMI acknowledge the following agencies for funding: DST, CSIR and UGC, New Delhi, India.

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Authors and Affiliations

  1. Department of Chemistry, University of Kalyani, Kalyani, Nadia, 741235, WB, India

    Manirul Islam, Sanchita Mondal, Paramita Mondal, Anupam Singha Roy, Dildar Hossain & Manir Mobarak

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  1. Manirul Islam
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  2. Sanchita Mondal
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  3. Paramita Mondal
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Correspondence to Manirul Islam.

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Islam, M., Mondal, S., Mondal, P. et al. Open air O-arylation reaction of phenols with aryl halides catalyzed by polymer-anchored copper(II) complexes. Transition Met Chem 36, 1–11 (2011). https://doi.org/10.1007/s11243-010-9426-2

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