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Synfacts 2020; 16(02): 0202
DOI: 10.1055/s-0039-1691547
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phenoxathiin Derivatives Catalyzed by Copper Supported on OMS-2

Contributor(s):
Yasuhiro Uozumi
,
Yuya Sugiyama
Liu N, Chao F, Huang Y, Wang Y, Meng X, Wang L. * Liu X. * China Three Gorges University, Yichang, P. R. of China
Highly Efficient CuO x /OMS-2 Catalyst for Synthesis of Phenoxathiin Derivatives via Intramolecular Arylations of Phenols with Aryl Halides.

Tetrahedron Lett. 2019;
60
DOI: 10.1016/j.tetlet.2019.151259
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Publication History

Publication Date:
21 January 2020 (online)

 
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Key words

copper catalysis - manganese oxide - octahedral molecular sieves - cyclization - phenoxathiins

Significance

Copper supported on manganese oxide based octahedral molecular sieves (CuO x /OMS-2) was prepared by reaction of OMS-2 with Cu(NO3)2·H2O (eq. 1). CuO x /OMS-2 catalyzed the intramolecular cyclization of 2-[(2-halophenyl)sulfanyl]phenols in the presence of Cs2CO3 at 130 °C to give the corresponding phenoxathiin derivatives in ≤95% yield (eq. 2).


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Comment

The authors have previously reported the preparation of CuO x /OMS-2 and its use in the synthesis of 3-iodoimidazo[1,2-a]pyridines (Catal. Sci. Technol. 2015, 5, 372). CuO x /OMS-2 was characterized by means of ICP-OES and TEM analyses. In the reaction of 2-[(2-bromophenyl)sulfanyl)-5-chlorophenol, the catalyst was recovered by simple filtration and reused seven times without significant loss of its catalytic activity.


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