Selective Aromatic C-H Hydroxylation Enabled by η 6-Coordination to Iridium(III)

D'Amato, E. M; Neumann, C. N.; Ritter, Tobias

doi:10.1021/acs.organomet.5b00731

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Selective Aromatic C-H Hydroxylation Enabled by η ⁶-Coordination to Iridium(III)

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Ritter, Tobias
Harvard Univ, Dept Chem & Chem Biol;
Research Department Ritter, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

D'Amato, E. M., Neumann, C. N., & Ritter, T. (2015). Selective Aromatic C-H Hydroxylation Enabled by η ⁶-Coordination to Iridium(III). Organometallics, 34(18), 4626-4631. doi:10.1021/acs.organomet.5b00731.

Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-9FF8-1

Abstract

We report an aromatic C–H hydroxylation protocol in which the arene is activated through η⁶-coordination to an iridium(III) complex. η⁶-Coordination of the arene increases its electrophilicity and allows for high positional selectivity of hydroxylation at the site of least electron density. Through investigation of intermediate η⁵-cyclohexadienyl adducts and arene exchange reaction, we evaluate incorporation of arene π-activation into a catalytic cycle for C–H functionalization.