Iridium(III)-bis(oxazolinyl)phenyl catalysts for enantioselective C–H functionalization

Clayton Owens, Adrián Varela-Álvarez, Vyacheslav Boyarskikh, Djamaladdin G. Musaev, Huw M. L. Davies, Simon B. Blakey

Chemical Science,
2013, 2590-2596; 10.1039/C3SC50886B


This collaborative project brings together three faculty members from the Center to design, prepare and apply a new Iridium(II)-based catalyst in carbene C-H Functionalization. The groups of Prof.'s Blakey, Musaev and Davies, all based at Emory, came together to help develop this novel catalytic system. Based on an established interest in Ir(III)-catalysis the Blakey prepared a catalyst based upon the PheBox ligand system.

These catalysts proved to be very effective at stabilizing acceptor carbenes, previously found to be highly unstable and too reactive to perform selective inter-molecular C-H Functionalization. However this catalyst system has shown high levels of regio- and stereocontrol with these reactive substrates.

Furthermore, theoretical studies performed by the Musaev group have proposed that the metal-bound carbene adopts an axial position, which explains the experimentally observed selectivities. This finding could have significant implications for future catalysts based on this ligand manifold.

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