Inorganic-organic hybrid double sulfates as catalysts of the diastereoselective nitroaldol reaction

Omar Kammoun (1, 2) , Walid Rekik (1) , Thierry Bataille (2) , Kamran T. Mahmudov (3, 4) , Maximilian N. Kopylovich (3) , Houcine Naïli (1)

1 L.E.S. - Laboratoire physico-chimie de l'Etat Solide
2 ISCR - Institut des Sciences Chimiques de Rennes
3 CQE - Centro de Quimica Estrutural
4 Baku State University, Department of Chemistry

Bis(1-phenylethanaminium) disulfatotetraaquazincate(II) dihydrate (C8H12N)2[Zn(H2O)4(SO4)2]*2H2O (1), bis(1H-benzo[d]imidazolium) hexaaquazinc(II) bis(sulfate) tetrahydrate (C7H7N2)2[Zn(H2O)6](SO4)2*4H2O (2) and bis(2-methyl-1H-imidazolium) hexaaquazinc(II) bis(sulfate) dihydrate (C4H7N2)2[Zn(H2O)6](SO4)2*2H2O (3) have been synthesized and fully structurally characterized including single-crystal X-ray diffraction analysis. 1-3 are organically templated hybrid layered materials comprising aquazinc(II) and aminium cations and sulfate anions. 1-3 are effective catalysts in the asymmetric Henry reaction; 1 being the most efficient one (yields up to 85% and threo/erythro diastereoselectivity up to 89:11).

Keywords: Hybrid materials; Double salts; Crystal structures; Henry reaction; Diastereoselectivity

Domains: Chemical Sciences; Other

Omar Kammoun, Walid Rekik, Thierry Bataille, Kamran T. Mahmudov, Maximilian N. Kopylovich, et al.. Inorganic-organic hybrid double sulfates as catalysts of the diastereoselective nitroaldol reaction. Journal of Organometallic Chemistry, 2013, 741-742, pp.136-140. ⟨10.1016/j.jorganchem.2013.05.028⟩. ⟨hal-00860183⟩