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67367-33-3

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A tautomeric ligand enables directed C-H hydroxylation with molecular oxygen
Hydroxylation of aryl carbon-hydrogen bonds with transition metal catalysts has proven challenging when oxygen is used as the oxidant. Here, we report a palladium complex bearing a bidentate pyridine/ pyridone ligand that efficiently catalyzes this reaction at ring positions adjacent to carboxylic acids. Infrared, x-ray, and computational analysis support a possible role of ligand tautomerization from monoanionic (L,X) to neutral (L,L) coordination in the catalytic cycle of aerobic carbon-hydrogen hydroxylation reaction. The conventional site selectivity dictated by heterocycles is overturned by this catalyst, thus allowing late-stage modification of compounds of pharmaceutical interest at previously inaccessible sites.
Li, Zhen,Wang, Zhen,Chekshin, Nikita,Qian, Shaoqun,Qiao, Jennifer X.,Cheng, Peter T.,Yeung, Kap-Sun,Ewing, William R.,Yu, Jin-Quan
p. 1452 - 1457
(2021/06/30)

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Chemical Properties

Melting Point: 263-265 °C
Boiling Point: 311.056 °C at 760 mmHg
Flash Point:141.922 °C
Density: 1.346 g/cm³
Storage Temp.:Inert atmosphere,Room Temperature
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.555
PKA: 0.26±0.10(Predicted)
PSA: 70.42000
LogP: 0.79380

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