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Synfacts 2015; 11(12): 1327
DOI: 10.1055/s-0035-1560887
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ullmann-Type Coupling of Phenols with Aryl Halides on Cuprian Zeolite USY

Contributor(s):
Yasuhiro Uozumi
,
Takao Osako
Magné V, Garnier T, Danel M, Pale P, * Chassaing S. * Université de Toulouse and Université de Strasbourg, France
CuI-USY as a Ligand-Free and Recyclable Catalytic System for the Ullmann-Type Diaryl Ether Synthesis.

Org. Lett. 2015;
17: 4494-4497
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Publication History

Publication Date:
17 November 2015 (online)

 
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Key words

copper - zeolites - Ullmann reaction - phenols - aryl halides

Significance

Copper(I)-exchanged zeolite USY (CuI-USY) catalyzed the Ullmann-type coupling of phenols with aryl iodides or bromides in the presence of cesium carbonate to give the corresponding diaryl ethers in up to 86% yield. In the reaction of 3,5-dimethylphenol with iodobenzene, the catalyst was recovered by simple filtration and reused four times without loss of catalytic activity.


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Comment

The authors have previously reported a Huisgen cycloaddition and a Glaser coupling with CuI-USY (Org. Lett. 2007, 9, 883; Eur. J. Org. Chem. 2009, 423). The catalytic activity of CuI-USY for the Ullmann-type coupling was superior to that of the other Cu(I) zeolites, such as CuI-MOR, CuI-β, or CuI-ZSM5. CuI-USY was ineffective for the reactions of 4-cyano- or 4-nitrophenols with phenyl halides. ICP-AES analysis revealed that no copper leached from the catalyst during the reaction.


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