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Lachkar D, Vilona D, Dumont E, et al. Grafting of Secondary Diolamides onto [P2 W15 V3 O62 ](9-) Generates Hybrid Heteropoly Acids. Angew Chem Int Ed Engl. 2016;55(20):5961-5doi: 10.1002/anie.201510954.
Lachkar, D., Vilona, D., Dumont, E., Lelli, M., & Lacôte, E. (2016). Grafting of Secondary Diolamides onto [P2 W15 V3 O62 ](9-) Generates Hybrid Heteropoly Acids. Angewandte Chemie (International ed. in English), 55(20), 5961-5. https://doi.org/10.1002/anie.201510954
Lachkar, David, et al. "Grafting of Secondary Diolamides onto [P2 W15 V3 O62 ](9-) Generates Hybrid Heteropoly Acids." Angewandte Chemie (International ed. in English) vol. 55,20 (2016): 5961-5. doi: https://doi.org/10.1002/anie.201510954
Lachkar D, Vilona D, Dumont E, Lelli M, Lacôte E. Grafting of Secondary Diolamides onto [P2 W15 V3 O62 ](9-) Generates Hybrid Heteropoly Acids. Angew Chem Int Ed Engl. 2016 May 10;55(20):5961-5. doi: 10.1002/anie.201510954. Epub 2016 Apr 08. PMID: 27061016.
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Angew Chem Int Ed Engl. 2016 May 10;55(20):5961-5. doi: 10.1002/anie.201510954. Epub 2016 Apr 08.

Grafting of Secondary Diolamides onto [P2 W15 V3 O62 ](9-) Generates Hybrid Heteropoly Acids.

Angewandte Chemie (International ed. in English)

David Lachkar, Debora Vilona, Elise Dumont, Moreno Lelli, Emmanuel Lacôte

Affiliations

  1. ICSN CNRS, 1 avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France.
  2. Univ Lyon, CPE Lyon, Université Claude Bernard Lyon1, CNRS, Institut de chimie de Lyon, C2P2 UMR 5265, 69616, Villeurbanne, France.
  3. Univ Lyon, Université Claude Bernard Lyon1, ENS Lyon, CNRS, Institut de chimie de Lyon, ISA-CRMN UMR 5280, 69100, Villeurbanne, France.
  4. Uni Lyon, ENS de Lyon, CNRS, Université Lyon 1, Laboratoire de chimie, UMR 5182, 69342, Lyon, France.
  5. Uni Lyon, ENS de Lyon, CNRS, Université Lyon 1, Laboratoire de chimie, UMR 5182, 69342, Lyon, France. [email protected].
  6. Univ Lyon, Université Claude Bernard Lyon1, ENS Lyon, CNRS, Institut de chimie de Lyon, ISA-CRMN UMR 5280, 69100, Villeurbanne, France. [email protected].
  7. ICSN CNRS, 1 avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France. [email protected].
  8. Univ Lyon, CPE Lyon, Université Claude Bernard Lyon1, CNRS, Institut de chimie de Lyon, C2P2 UMR 5265, 69616, Villeurbanne, France. [email protected].

PMID: 27061016 DOI: 10.1002/anie.201510954

Abstract

The Dawson tungstovanadate [P2 W15 V3 O62 ](9-) can be grafted to secondary diolamides. The electron-withdrawing character of the polyanion increases the acidity of the amide proton, leading to an organo-polyoxometalate, which can be used as a Brønsted organocatalyst. High-field NMR and DFT modeling indicate that the amide proton stays on the nitrogen and that the exalted acidity derives from the interaction between the organic and inorganic parts of the organo-polyoxometalate. The amide-inserted vanadotungstates thus form a new family of (hybrid) heteropolyacids, offering new perspectives for the application of POM-based catalysis in organic synthesis.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: acid derivatives; hydrogen transfer; organic-inorganic hybrid composites; organocatalysis; polyoxometalates

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