Organic–inorganic supramolecular solid catalyst boosts organic reactions in water

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.

Catalytic Transfer Hydrogenation of Biomass‐Derived Carbonyls over Hafnium‐Based Metal–Organic Frameworks

“…MOFs have been explored for a broad range of catalytic transformations. Reported examples are condensation, ring opening, cycloaddition, N ‐alkylation, isomerization, hydrogenation, oxidation, and carbene reactions. MOF‐based materials are suitable catalysts for the production of certain fine chemicals .…”

Recent applications of isatin in the synthesis of organic compounds

“…115 This reaction has been widely studied and different catalysts such as [Amb]L-prolinate, 116 tetrabutylammonium bromide (TBAB), 117 boron nitride supported iron oxide (BN@Fe3O4), 118 AI-ITQ-HB, 119 [bmim]OH, 120 Fe3O4, 121 carbon nanotube (CNT), 122 NaOAc, 123 CuFe2O4 nanoparticles 124 and trisodium citrate dihydrate 125 were used in this reaction.…”

A Mini-Review on Organic synthesis in Water

“…Organic synthesis reactions on water at the organic-liquid water interface were studied by Butler et al [27]. García-García et al [28] have reported 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 [28].…”