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. 2021 Dec 20;27(71):17761-17764.
doi: 10.1002/chem.202102807. Epub 2021 Nov 5.

Organo-Polyoxometalate-Based Hydrogen-Bond Catalysis

Debora Vilona  1   2   3 , Moreno Lelli  2   4 , Elise Dumont  3 , Emmanuel Lacôte  1
Affiliations

Organo-Polyoxometalate-Based Hydrogen-Bond Catalysis

Debora Vilona et al. Chemistry. .

Abstract

Several urea-inserted organo-polyoxometalates (POMs) derived from polyoxotungstovanadate [P2 V3 W15 O61 ]9- were prepared. The insertion of the carbonyl into the polyoxometallic framework activates the urea toward Hydrogen-bond catalysis. This was shown on the Friedel-Crafts arylation of trans-β-nitrostyrene. Modelling shows that the most stable form of the organo-POMs features a cis-trans arrangement of the two N-H bonds, but that the likely catalytically active trans-trans form is accessible at room temperature. Finally, it is possible that the oxo substituents next to the vanadium atoms may help the approach of the nucleophile via H-bonding.

Keywords: cooperative effects; hydrogen bonds; organic-inorganic hybrid composites; organocatalysis; polyoxometalates.

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