Anchoring of Chiral Manganese(III) Salen Complex onto Organo Clay and Porous Clay Heterostructure and Catalytic Activity in Alkene Epoxidation

摘要

The chiral Mn(III) salen complex (C1) was immobilised onto a natural clay (BEN) and a porous clay heterostructure (PCH) functionalised with 3-aminopropyl-triethoxysilane (APTES). FTIR, XPS and Mn chemical analysis confirm the C1 anchorage in both materials, but with higher efficiency in BEN_APTES clay. The catalytic activity of C1@BEN_APTES and C1@PCH_APTES, was assessed in the epoxidation of styrene (sty) and α-methylstyrene (∝-Mesty) using NaOCl and m-chloro-peroxybenzoic acid (m-CPBA)/N-methylmorpholine-N-oxide (NMO). Both materials behave as moderate catalysts, show high epoxide selectivity but low enantiomeric excesses. In the case of sty epoxidation with m-CBPA/NMO the C1@PCH_APTES catalyst showed the highest catalytic activity, whereas in ∝-Mesty epoxidation, the C1@PCH_APTES catalyst, although leading to lower substrate conversion than the BEN analogue, presented the lowest complex leaching. In all cases, the oxidant NaOCl had some destructive effect in the hybrid catalysts, highlighting the importance of a careful choice of catalyst and oxidant system.