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Ligand functionalization as a deactivation pathway in a fac-Ir(ppy)3-mediated radical addition

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Abstract

Knowledge of the kinetic behavior of catalysts under synthetically relevant conditions is vital for the efficient use of compounds that mediate important transformations regardless of their composition or driving force. In particular, these data are of great importance to add perspective to the growing number of applications of photoactive transition metal complexes. Here we present kinetic, synthetic, and spectroscopic evidence of the mechanistic behavior of fac-Ir(ppy)3 in a visible light-mediated radical addition to 3-methylindole, demonstrating the instability of fac-Ir(ppy)3 under these conditions. During the reaction, rapid in situ functionalization of the photocatalyst occurs, eventually leading to deactivation. These findings demonstrate a conceivable deactivation process for catalytic single electron reactions in the presence of radicophilic ligands. Attempts to inhibit photocatalyst deactivation through structural modification provide further insight into catalyst selection for a given system of interest.

Graphical abstract: Ligand functionalization as a deactivation pathway in a fac-Ir(ppy)3-mediated radical addition

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Article information


Submitted
06 Oct 2014
Accepted
20 Oct 2014
First published
20 Oct 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 537-541
Article type
Edge Article
Author version available

Ligand functionalization as a deactivation pathway in a fac-Ir(ppy)3-mediated radical addition

J. J. Devery III, J. J. Douglas, J. D. Nguyen, K. P. Cole, R. A. Flowers II and C. R. J. Stephenson, Chem. Sci., 2015, 6, 537
DOI: 10.1039/C4SC03064H

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    [Original citation] - Published by The Royal Society of Chemistry.

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