Recyclable Acid–Base Bifunctional Core–Shell–Shell Nanosphere Catalyzed Synthesis of 5‐Aryl‐1H‐1,2,3‐triazoles through the “One‐Pot” Cyclization of Aldehydes, Nitromethane, and Sodium Azide

A magnetically separable core–shell–shell nanosphere, Fe3O4@nSiO2‐SO3H@MS‐NHCOCH3 (n=nonporous, MS=microporous SiO2), was fabricated as an acid–base collaborative catalyst for the three‐component cyclization of aromatic aldehydes, nitroalkane, and sodium azide to afford 1H‐1,2,3‐triazoles. The bifun...

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Bibliographic Details
Published in:ChemCatChem 2017-08, Vol.9 (16), p.3131-3137
Main Authors: Liu, Lei, Ai, Yongjian, Li, Dong, Qi, Li, Zhou, Junjie, Tang, Zhike, Shao, Zixing, Liang, Qionglin, Sun, Hong‐Bin
Format: Article
Language:English
Subjects:
Acetic acid
Aldehydes
Ammonium acetate
Aromatic compounds
bifunctional catalysts
Catalysts
Chemical synthesis
heterogeneous catalysis
Iron oxides
Magnetic fields
multicomponent reactions
Nanospheres
nanostructures
nitrogen heterocycles
Nitromethane
Silicon dioxide
Sodium
Triazoles
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Summary:A magnetically separable core–shell–shell nanosphere, Fe3O4@nSiO2‐SO3H@MS‐NHCOCH3 (n=nonporous, MS=microporous SiO2), was fabricated as an acid–base collaborative catalyst for the three‐component cyclization of aromatic aldehydes, nitroalkane, and sodium azide to afford 1H‐1,2,3‐triazoles. The bifunctional heterogeneous catalyst showed high activity for this transformation and good chemoselectivity, and toxic HN3 was not released during the course of the reaction. A variety of aldehydes were transformed into the corresponding 5‐aryl‐1H‐1,2,3‐triazoles in up to 98 % yield. Furthermore, the catalyst could be recovered by using an external magnetic field and reused many times without any loss in activity. In contrast, a homogeneous catalyst system comprising ammonium acetate/acetic acid also worked in this three‐component cyclization to afford 1H‐1,2,3‐triazoles. Tri, tri, tri again: Fe3O4@nSiO2‐SO3H@MS‐NHCOCH3 (n=nonporous, MS=microporous SiO2) is an efficient, heterogeneous catalyst for the formation of 1H‐1,2,3‐triazoles from aromatic aldehydes, nitromethane, and sodium azide. Few byproducts are formed, and the reaction is safe to handle, as dangerous hydrazoic acid is not released. The catalyst can be reused up to 10 times without any loss in catalytic activity.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201700401