Masferrer-Rius, Eduard published the artcileAromatic C-H Hydroxylation Reactions with Hydrogen Peroxide Catalyzed by Bulky Manganese Complexes, Product Details of C9H12O, the publication is Advanced Synthesis & Catalysis (2021), 363(15), 3783-3795, database is CAplus.
The oxidation of aromatic substrates to phenols with H2O2 as a benign oxidant remains an ongoing challenge in synthetic chem. Herein, the authors successfully achieved to catalyze aromatic C-H bond oxidations using a series of biol. inspired manganese catalysts in fluorinated alc. solvents. While introduction of bulky substituents into the ligand structure of the catalyst favors aromatic C-H oxidations in alkylbenzenes, oxidation occurs at the benzylic position with ligands bearing electron-rich substituents. Therefore, the nature of the ligand is key in controlling the chemoselectivity of these Mn-catalyzed C-H oxidations Introduction of bulky groups into the ligand prevents catalyst inhibition through phenolate-binding, consequently providing higher catalytic turnover numbers for phenol formation. Furthermore, employing halogenated carboxylic acids in the presence of bulky catalysts provides enhanced catalytic activities, which can be attributed to their low pKa values that reduces catalyst inhibition by phenolate protonation as well as to their electron-withdrawing character that makes the manganese oxo species a more electrophilic oxidant. Moreover, to the best of the authors’ knowledge, the new system can accomplish the oxidation of alkylbenzenes with the highest yields so far reported for homogeneous arene hydroxylation catalysts. Overall the authors’ data provide a proof-of-concept of how Mn(II)/H2O2/RCO2H oxidation systems are easily tunable by the solvent, carboxylic acid additive, and steric demand of the ligand. The chemo- and site-selectivity patterns of the current system, a negligible KIE, the observation of an NIH-shift, and the effectiveness of using tBuOOH as oxidant overall suggest that hydroxylation of aromatic C-H bonds proceeds through a metal-based mechanism, with no significant involvement of hydroxyl radicals, and via an arene oxide intermediate.
Advanced Synthesis & Catalysis published new progress about 645-56-7. 645-56-7 belongs to alcohols-buliding-blocks, auxiliary class Liquid Crystal &OLED Materials, name is 4-Propylphenol, and the molecular formula is C9H12O, Product Details of C9H12O.
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