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Highly Selective and Efficient Ring Hydroxylation of Alkylbenzenes with Hydrogen Peroxide and an Osmium(VI) Nitrido Catalyst.

Authors :
Kwong HK
Lo PK
Yiu SM
Hirao H
Lau KC
Lau TC
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2017 Sep 25; Vol. 56 (40), pp. 12260-12263. Date of Electronic Publication: 2017 Aug 23.
Publication Year :
2017

Abstract

The Os <superscript>VI</superscript> nitrido complex, Os <superscript>VI</superscript> (N)(quin) <subscript>2</subscript> (OTs) (1, quin=2-quinaldinate, OTs=tosylate), is a highly selective and efficient catalyst for the ring hydroxylation of alkylbenzenes with H <subscript>2</subscript> O <subscript>2</subscript> 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 <superscript>VIII</superscript> nitrido oxo species.<br /> (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3773
Volume :
56
Issue :
40
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
28734083
Full Text :
https://doi.org/10.1002/anie.201705986