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Imidazolium-based organoiridium-functionalized periodic mesoporous organosilica boosts enantioselective reduction of α-cyanoacetophenones, α-nitroacetophenones, and β-ketoesters

An imidazolium-based, organoiridium-functionalized periodic mesoporous organosilica is developed through complexation of chiral pentafluorophenylsulfonyl-1,2-diphenylethylenediamine and organoiridium-functionalized periodic mesoporous organosilica. Structural analyses and characterizations of catalyst reveal well-defined single-site iridium active species within its organosilicate network. Electron microscopy confirms a highly ordered dimensional-hexagonal mesostructure. This bifunctional heterogeneous catalyst displays excellent catalytic performance in the enantioselective reduction of α-cyano and α-nitroacetophenones. As expected, incorporation of imidazolium-functionality within hydrophobic periodic mesoporous organosilica promotes catalytic activity and enantioselectivity. In addition, this heterogeneous catalyst can be recovered and reused for at least eight times without loss of its catalytic activity. Furthermore, the approach described here can also construct another organoiridium-functionalized periodic mesoporous organosilica through postcoordination of chiral methylsulfonyl-1,2-diphenylethylenediamine, which provides excellent catalytic activity and enantioselectivity in the enantioselective reduction of β-ketoesters. The method presented here offers a potential way for immobilizing various chiral ligands to construct chiral organometal-functionalized periodic mesoporous organosilicas.

Iron catalyzed asymmetric hydrogenation of ketones

Chiral molecules, such as alcohols, are vital for the manufacturing of fine chemicals, pharmaceuticals, agrochemicals, fragrances, and novel materials. These molecules need to be produced in high yield and high optical purity and preferentially catalytically. Among all the asymmetric catalytic reactions, asymmetric hydrogenation with H2 (AH) is the most widely used in the industry. With few exceptions, these AH processes use catalysts based on the three critical metals, rhodium, ruthenium, and iridium. Herein we describe a simple, industrially viable iron catalyst that allows for the AH of ketones, a process currently dominated by ruthenium and rhodium catalysts. By combining a chiral, 22-membered macrocyclic ligand with the cheap, readily available Fe 3(CO)12, a wide variety of ketones have been hydrogenated under 50 bar H2 at 45-65 C, affording highly valuable chiral alcohols with enantioselectivities approaching or surpassing those obtained with the noble metal catalysts. In contrast to AH by most noble metal catalysts, the iron-catalyzed hydrogenation appears to be heterogeneous.

Imidazolium-based organoiridium-functionalized periodic mesoporous organosilica boosts enantioselective reduction of α-cyanoacetophenones, α-nitroacetophenones, and β-ketoesters

An imidazolium-based, organoiridium-functionalized periodic mesoporous organosilica is developed through complexation of chiral pentafluorophenylsulfonyl-1,2-diphenylethylenediamine and organoiridiumfunctionalized periodic mesoporous organosilica. Structural analyses and characterizations of catalyst reveal well-defined single-site iridium active species within its organosilicate network. Electron microscopy confirms a highly ordered dimensional-hexagonal mesostructure. This bifunctional heterogeneous catalyst displays excellent catalytic performance in the enantioselective reduction of α-cyano and α-nitroacetophenones. As expected, incorporation of imidazolium-functionality within hydrophobic periodic mesoporous organosilica promotes catalytic activity and enantioselectivity. In addition, this heterogeneous catalyst can be recovered and reused for at least eight times without loss of its catalytic activity. Furthermore, the approach described here can also construct another organoiridium-functionalized periodic mesoporous organosilica through postcoordination of chiral methylsulfonyl-1,2-diphenylethylenediamine, which provides excellent catalytic activity and enantioselectivity in the enantioselective reduction of β-ketoesters. The method presented here offers a potential way for immobilizing various chiral ligands to construct chiral organometal-functionalized periodic mesoporous organosilicas.