From homogeneously to heterogeneously catalyzed cyclopropanation reactions: New polymeric membranes embedding cobalt chiral schiff base complexes

In this paper we report the preparation of catalytic polymeric membranes having the complex [(N,N′-bis(3-tert-butyl-5-(heptadecafluorooctyl)salicylidene)-trans-1,2-cyclohexanediamine)Co] embedded into Hyflon AD60X, PES and PSf and their use in the cyclopropanation reaction of olefins with ethyl diazoacetate (EDA). A study of the reaction in the homogeneous phase was also performed. The kinetics of the cyclopropanation reaction is first-order in the diazoacetate and the catalyst and zero order in the olefin, but we observed a more complex dependence on the additive, NMI (N-methylimidazole). The positive effect of the additive is completely reversed at NMI concentration higher than 6·10−2 M.

Graphical abstractThe new catalytic membranes having the complex [(N,N′-bis(3-tert-butyl-5-(heptadecafluorooctyl)salicylidene)-trans-1,2-cyclohexanediamine)Co] embedded into Hyflon AD60X, PES and PSf have been prepared and characterized and their use in the cyclopropanation reaction of olefins with ethyl diazoacetate (EDA) is reported.Figure optionsDownload full-size imageDownload high-quality image (73 K)Download as PowerPoint slide