Enzymes show the remarkable ability to stabilize reactive metal species (such as oxo-Fe(IV)); which are able to catalyze, otherwise challenging, reactions such as the oxidation of C-H bonds. Moreover, their internal cavities introduce a greater degree of selectivity since only properly-sized substrates can bind in positions close enough to the catalytic metal to be affected. Unfortunately, enzymes with specific functions are not easily synthesized in vitro. In order to mimic biological hydrocarbon oxidation we turned to the use of cavitands. Cavitands are synthetic molecular receptors that have found great success in supramolecular chemistry and guest recognition. This work aims to use the host-guest properties of cavitands to perform regioselective C-H oxidations under mild conditions. Performing C-H oxidations in biomimetic catalysis can be accomplished by coordinating octahedral iron with a single tetradentate amine ligand which would provide strong electron donation to the iron metal providing stabilization while forcing two orbitals into a cis conformation for oxidation.

Biomimetic C-H oxidation catalysis via self-assembly metal coordinated cavitand

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.