Al-containing mesoporous carbon as effective catalysts for the chemoselective reduction of carbon–carbon double bonds in nitrostilbene derivatives

Abstract

A series of Al, Mn, Cu and Fe metal-containing mesoporous carbon catalysts were synthesized for catalyzing selective reduction of carbon–carbon double bond in 4-nitrostilbene analogs bearing nitro group with hydrazine hydrate. The results indicated that the reduction reaction was able to be achieved successfully between carbon–carbon double bond and nitro group. The efficient method has been developed for the reduction of CC double bonds with diimide, catalytically generated in situ from hydrazine hydrate by the synthesized catalysts. The 0.15Al–MC1 as heterogeneous catalyst exhibited the highest catalysis activity and chemoselectivity in all synthesized catalysts. In the presence of 0.15Al–MC1, the reduction of carbon–carbon double bond in 4-nitrostilbene derivatives was up to 99% yield and >99% chemoselectivity at 70°C in ethanol. On the other hand, the high selective reduction of nitro group in 4-nitrostilbenes was also facile to be achieved with hydrazine hydrate, active carbon and FeCl3·6H2O under inert atmosphere.