Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 23, Pages 9155-9159Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b02864
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Funding
- NRF of Korea through CRI [NRF-2012R1A3A2048842]
- Basic Science Research Program [2017R1D1A1B03029982, 2017R1D1A1B03032615]
- MEXT [16H02268]
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Photocatalytic oxygenation of hexamethylbenzene occurs under visible-light irradiation of an O(2)(-)saturated acetonitrile solution containing a cobalt porphyrin complex Co-II(TPP) (TPP2 = tetraphenylporphyrin dianion), water, and triflic acid (HOTf) via a one-photon-two-electron process, affording pentamethylbenzyl alcohol and hydrogen peroxide as products with a turnover number of >6000; in this reaction, H2O and O-2 were used as an oxygen source and a two-electron oxidant, respectively. The photocatalytic mechanism was clarified by means of electron paramagnetic resonance, time-resolved fluorescence, and transient absorption measurements as well as O-18-labeling experiments with (H2O)-O-18 and O-18(2). To the best of our knowledge, we report the first example of efficient photocatalytic oxygenation of an organic substrate by a metal complex using H2O as an oxygen source and O-2 as a two-electron oxidant.
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