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Highly Selective and Efficient Ring Hydroxylation of Alkylbenzenes with Hydrogen Peroxide and an Osmium(VI) Nitrido Catalyst
Author(s) -
Kwong HoiKi,
Lo PoKam,
Yiu ShekMan,
Hirao Hajime,
Lau KaiChung,
Lau TaiChu
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705986
Subject(s) - alkylbenzenes , hydroxylation , chemistry , mesitylene , ethylbenzene , hydrogen peroxide , catalysis , ring (chemistry) , osmium , medicinal chemistry , density functional theory , organic chemistry , ruthenium , computational chemistry , enzyme
The Os VI nitrido complex, Os VI (N)(quin) 2 (OTs) ( 1 , quin=2‐quinaldinate, OTs=tosylate), is a highly selective and efficient catalyst for the ring hydroxylation of alkylbenzenes with H 2 O 2 at room temperature. Oxidation of various alkylbenzenes occurs with ring/chain oxidation ratios ranging from 96.7/3.3 to 99.9/0.1, and total product yields from 93 % to 98 %. Moreover, turnover numbers up to 6360, 5670, and 3880 can be achieved for the oxidation of p‐xylene, ethylbenzene, and mesitylene, respectively. Density functional theory calculations suggest that the active intermediate is an Os VIII nitrido oxo species.