Tandem reactions are drawing increasing attention to maximize process efficiency by avoiding intermediate product purifications in multi-step syntheses. The operation of multiple catalytic reactions in one pot is often limited by incompatibilities of the catalysts and reaction conditions. Inspired by nature where the compartmentalization of cells enables metabolism pathways to proceed simultaneously, we have designed and synthesized metal catalyst containing shell cross-linked micelles (SCMs) that enable the site isolation of two incompatible catalytic systems. The SCMs were prepared from amphiphilic poly(2-oxazoline) triblock copolymers with orthogonal functional handles in the side-chains in hydrophobic and hydrophilic blocks to attach the metal catalysts and a cross-linkable middle block to stabilize the micelle structure from disassembly.  As a test system, we immobilized Ru(II)-porphyrin and Co(III)-salen complexes in the shell and in the core respectively for tandem catalytic reactions. The first step of the tandem reaction is the Ru(II)-porphyrin-catalyzed epoxidation of terminal olefins and the second step is the Co(III)-salen-catalyzed hydrolytic kinetic resolution (HKR) of the racemic epoxide intermediate.

Shell cross-linked micelle supported catalysts for tandem reactions

248th National Meeting (2014)

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