A CO 2 -mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO 2 -mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO 2 ( e.g. , azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the an...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2021-12, Vol.23 (24), p.9870-9875
Hauptverfasser: Tang, Minhao, Zhang, Fengtao, Zhao, Yanfei, Wang, Yuepeng, Ke, Zhengang, Li, Ruipeng, Zeng, Wei, Han, Buxing, Liu, Zhimin
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Sprache:eng
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Zusammenfassung:Herein, we report a CO 2 -mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO 2 ( e.g. , azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO 2 could abstract one proton from proton resources ( e.g. , IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO 2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.
ISSN:1463-9262
1463-9270
DOI:10.1039/D1GC03865F