Journal of the American Chemical Society, volume 144, issue 39, pages 18109-18116
Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature
2
Small Molecule Drug Discovery, Bristol Myers Squibb Research and Early Development, P.O. Box 4000, Princeton, New Jersey 08543, United States
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3
Small Molecule Drug Discovery, Bristol Myers Squibb Research and Early Development, 100 Binney Street, Cambridge, Massachusetts 02142, United States
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Publication type: Journal Article
Publication date: 2022-09-22
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
With the large number of Pd(II)-catalyzed C-H activation reactions of native substrates developed in the past decade, the development of catalysts to enable the use of green oxidants under safe and practical conditions has become an increasingly important challenge. Notably, the compatibility of Pd(II) catalysts with sustainable aqueous H2O2 has been a long-standing challenge in catalysis including Wacker-type oxidations. We report herein a bifunctional bidentate carboxyl-pyridone (CarboxPyridone) ligand that enables room-temperature Pd-catalyzed C-H hydroxylation of a broad range of benzoic and phenylacetic acids with an industry-compatible oxidant, aqueous hydrogen peroxide (35% H2O2). The scalability of this methodology is demonstrated by a 1000 mmol scale reaction of ibuprofen (206 g) using only a 1 mol % Pd catalyst loading. The utility of this protocol is further illustrated through derivatization of the products and synthesis of polyfluorinated natural product coumestan and pterocarpene from phenol intermediates prepared using this methodology.
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Citations by publishers
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12 publications, 33.33%
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1 publication, 2.78%
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1 publication, 2.78%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Li Z. et al. Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature // Journal of the American Chemical Society. 2022. Vol. 144. No. 39. pp. 18109-18116.
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Li Z., Park H., Qiao J. X., Yeung K., Yu J. Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature // Journal of the American Chemical Society. 2022. Vol. 144. No. 39. pp. 18109-18116.
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TY - JOUR
DO - 10.1021/jacs.2c08332
UR - https://doi.org/10.1021/jacs.2c08332
TI - Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature
T2 - Journal of the American Chemical Society
AU - Li, Zhen
AU - Park, Han-Seul
AU - Qiao, Jennifer X
AU - Yeung, Kap-Sun
AU - Yu, Jinquan
PY - 2022
DA - 2022/09/22 00:00:00
PB - American Chemical Society (ACS)
SP - 18109-18116
IS - 39
VL - 144
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2022_Li,
author = {Zhen Li and Han-Seul Park and Jennifer X Qiao and Kap-Sun Yeung and Jinquan Yu},
title = {Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature},
journal = {Journal of the American Chemical Society},
year = {2022},
volume = {144},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/jacs.2c08332},
number = {39},
pages = {18109--18116},
doi = {10.1021/jacs.2c08332}
}
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MLA
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Li, Zhen, et al. “Ligand-Enabled C–H Hydroxylation with Aqueous H2O2 at Room Temperature.” Journal of the American Chemical Society, vol. 144, no. 39, Sep. 2022, pp. 18109-18116. https://doi.org/10.1021/jacs.2c08332.