Organic–inorganic supramolecular solid catalyst boosts organic reactions in water

Pilar García-García, José María Moreno, Urbano Díaz, Marta Bruix and Avelino Corma ()
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Pilar García-García: Instituto de Tecnología Química, UPV-CSIC, Universidad Politécnica de Valencia
José María Moreno: Instituto de Tecnología Química, UPV-CSIC, Universidad Politécnica de Valencia
Urbano Díaz: Instituto de Tecnología Química, UPV-CSIC, Universidad Politécnica de Valencia
Marta Bruix: Instituto de Química Física Rocasolano, CSIC
Avelino Corma: Instituto de Tecnología Química, UPV-CSIC, Universidad Politécnica de Valencia

Nature Communications, 2016, vol. 7, issue 1, 1-9

Abstract: Abstract Coordination polymers and metal-organic frameworks are appealing as synthetic hosts for mediating chemical reactions. Here we report the preparation of a mesoscopic metal-organic structure based on single-layer assembly of aluminium chains and organic alkylaryl spacers. The material markedly accelerates condensation reactions in water in the absence of acid or base catalyst, as well as organocatalytic Michael-type reactions that also show superior enantioselectivity when comparing with the host-free transformation. The mesoscopic phase of the solid allows for easy diffusion of products and the catalytic solid is recycled and reused. Saturation transfer difference and two-dimensional 1H nuclear Overhauser effect NOESY NMR spectroscopy show that non-covalent interactions are operative in these host–guest systems that account for substrate activation. The mesoscopic character of the host, its hydrophobicity and chemical stability in water, launch this material as a highly attractive supramolecular catalyst to facilitate (asymmetric) transformations under more environmentally friendly conditions.

Date: 2016
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DOI: 10.1038/ncomms10835

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