Ionic Manganese Porphyrins with S-containing Counter Anions: Mimicking Cytochrome P450 Activity for Alkene Epoxidation

Abstract

The ionic manganese porphyrins, composed of trimethylbenzylammonium cations and S-containing anions, were designed to mimic cytochrome P450. S-containing anions could function as the stoichiometric axial ligands and counterions dually. Such ionic catalysts showed good catalytic performance in alkene epoxidation as compared with their neutral counterparts, in terms of activity, epoxide selectivity, and recyclability.

Biomimetic Catalysis

“…Most artificial P450 mimics replace the iron center with a more stable metal, such as manganese or rhodium . One example of an iron-containing mimic is shown in Figure .…”

Selective oxygenation of α-olefins by means of metalloporphyrin catalysts mimicking cytochrome P-450

“…The reaction product was filtrated out the reaction mixture and washed with dichloromethane, methanol, water, and methanol ( Fig. 1; catalysts [1][2][3][4][5][9][10][11] 15 .…”

“…There are two ways to prevent the deactivation: first, the application of a homogeneous catalysis -modification of the porphyrin skeleton with various bulky electronegative substituents and an axial bond with an appropriate ligand of the central atom [1][2][3][4][5][6][7][8][9] ; second, the use of a heterogeneous catalysis -an attachment of the catalysts to a suitable support. As a support cyclodextrin, cyclofan, molecular sieves, Merrifield resin or synthetic polymers can be used 10-12 . In our previous work 13 we have used the homogeneous catalysis with different metallocomplexes than porphyrin.…”

Mimicking the Cell: Bio-Inspired Functions of Supramolecular Assemblies

“…The structure is an excellent mimic of P450 , that was used for some oxidation reaction with high regioselectivity resembling the ones performed with the aid of natural P450. The iron center was also successfully exchanged with some other metals such as rhodium and manganese . Other reports have shown lucrative examples of cyclodextrins mimicking other artificial enzymes such as esterases, phospholipases, and nucleases …”

“…The iron center was also successfully exchanged with some other metals such as rhodium 472 and manganese. 473 Other reports have shown lucrative examples of cyclodextrins mimicking other artificial enzymes such as esterases, phospholipases, and nucleases. 468…”