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Synfacts 2025; 21(01): 62
DOI: 10.1055/a-2467-5897
Polymer-Supported Synthesis

Photocatalytic Cycloaddition and Oxidation by a Benzothiadiazole-Based Ordered Mesoporous Polymer

Contributor(s):
Yasuhiro Uozumi 
,
Kenji Tsukamoto
Liu J, Zhu Y, Li S, Hu Y, Chen K, Li T, Zhang S *. Lanzhou University, P. R. China
Benzothiadiazole-Based Ordered Mesoporous Polymer as a Versatile, Metal-Free Heterogeneous Photocatalyst.

Chem. Eur. J. 2024;
30: e202402040
DOI: 10.1002/chem.202402040
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Keywords

photocatalysis - [3+2] cycloaddition - aerobic oxidation - ordered mesoporous polymer - benzothiadiazoles - 2,3-dihydrobenzofurans - sulfoxides

Significance

A benzothiadiazole-based ordered mesoporous polymer (BT-OMP) was prepared according to equation 1. BT-OMP promoted the [3 + 2] cycloaddition of 4-alkoxyphenols with styrenes in the presence of (NH4)2S2O8 under blue light to give 2,3-dihydrobenzofurans 1 (15 examples) in up to 98 % yield (eq 2). BT-OMP also catalyzed the oxidation of sulfides under the photocatalytic conditions to afford sulfoxides (13 examples) in up to 99 % yield (eq 3).


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Comment

The mesoporous structure of the BT-OMP was confirmed by TEM images and nitrogen gas adsorption–desorption measurements. In the cycloaddition forming 1 (R1 = R3  = Me, R2  = H, R4 = OMe) and oxidation of thioanisole, the catalyst was recovered by centrifugation and reused seven times without significant loss of its catalytic activity. A hot filtration test supported heterogeneity of the catalytic system.


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Publication History

Article published online:
20 December 2024

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