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Ligand-Enabled C-H Hydroxylation with Aqueous H2O2 at Room Temperature

Zhen Li, Han Seul Park, Jennifer X. Qiao, Kap-Sun Yeung and Jin-Quan Yu*

*The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States, Email:

Z. Li, H. S. Park, J. X. Qiao, K.-S. Yeung, J.-Q. Yu, J. Am. Chem. Soc., 2022, 144, 18109-18116.

DOI: 10.1021/jacs.2c08332

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A bifunctional bidentate carboxyl-pyridone ligand enables a room-temperature Pd-catalyzed C-H hydroxylation of a broad range of benzoic and phenylacetic acids with aqueous hydrogen peroxide. The scalability of this methodology is demonstrated by a 1 mol scale reaction of ibuprofen using only a 1 mol % Pd catalyst loading.

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proposed mechanism

Pd(II)-Catalyzed Hydroxylation of Arenes with 1 atm of O2 or Air

Y.-H. Zhang, J.-Q. Yu, J. Am. Chem. Soc., 2009, 131, 14654-14655.

Key Words

hydroxylation, hydrogen peroxide

ID: J48-Y2022