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

Hoi-Ki Kwong; Po-Kam Lo; Shek-Man Yiu; Hajime Hirao; Kai-Chung Lau; Tai-Chu Lau

doi:10.1002/anie.201705986

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

Hoi-Ki Kwong, Po-Kam Lo, Shek-Man Yiu, Hajime Hirao^*, Kai-Chung Lau^*, Tai-Chu Lau^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

24 Citations (Scopus)

Abstract

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 H₂O₂ 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.

Original language	English
Pages (from-to)	12260-12263
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	40
Online published	23 Aug 2017
DOIs	https://doi.org/10.1002/anie.201705986
Publication status	Published - 25 Sept 2017

Research Keywords

alkylbenzenes
hydrogen peroxide
hydroxylation
nitrido
osmium complexes

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10.1002/anie.201705986

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title = "Highly Selective and Efficient Ring Hydroxylation of Alkylbenzenes with Hydrogen Peroxide and an Osmium(VI) Nitrido Catalyst",

abstract = "The OsVI nitrido complex, OsVI(N)(quin)2(OTs) (1, quin=2-quinaldinate, OTs=tosylate), is a highly selective and efficient catalyst for the ring hydroxylation of alkylbenzenes with H2O2 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 OsVIII nitrido oxo species.",

keywords = "alkylbenzenes, hydrogen peroxide, hydroxylation, nitrido, osmium complexes",

author = "Hoi-Ki Kwong and Po-Kam Lo and Shek-Man Yiu and Hajime Hirao and Kai-Chung Lau and Tai-Chu Lau",

year = "2017",

month = sep,

day = "25",

doi = "10.1002/anie.201705986",

language = "English",

volume = "56",

pages = "12260--12263",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley & Sons",

number = "40",

}

Highly Selective and Efficient Ring Hydroxylation of Alkylbenzenes with Hydrogen Peroxide and an Osmium(VI) Nitrido Catalyst. / Kwong, Hoi-Ki; Lo, Po-Kam; Yiu, Shek-Man et al.
In: Angewandte Chemie - International Edition, Vol. 56, No. 40, 25.09.2017, p. 12260-12263.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

TY - JOUR

T1 - Highly Selective and Efficient Ring Hydroxylation of Alkylbenzenes with Hydrogen Peroxide and an Osmium(VI) Nitrido Catalyst

AU - Kwong, Hoi-Ki

AU - Lo, Po-Kam

AU - Yiu, Shek-Man

AU - Hirao, Hajime

AU - Lau, Kai-Chung

AU - Lau, Tai-Chu

PY - 2017/9/25

Y1 - 2017/9/25

N2 - The OsVI nitrido complex, OsVI(N)(quin)2(OTs) (1, quin=2-quinaldinate, OTs=tosylate), is a highly selective and efficient catalyst for the ring hydroxylation of alkylbenzenes with H2O2 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 OsVIII nitrido oxo species.

AB - The OsVI nitrido complex, OsVI(N)(quin)2(OTs) (1, quin=2-quinaldinate, OTs=tosylate), is a highly selective and efficient catalyst for the ring hydroxylation of alkylbenzenes with H2O2 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 OsVIII nitrido oxo species.

KW - alkylbenzenes

KW - hydrogen peroxide

KW - hydroxylation

KW - nitrido

KW - osmium complexes

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U2 - 10.1002/anie.201705986

DO - 10.1002/anie.201705986

M3 - RGC 21 - Publication in refereed journal

SN - 1433-7851

VL - 56

SP - 12260

EP - 12263

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -

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

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GRF: Seven-Coordinate Metal Oxo and D0 Metal Nitrido Oxo Complexes as Active Species for the Oxidation of Water and Organic Substrates

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

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GRF: Seven-Coordinate Metal Oxo and D0 Metal Nitrido Oxo Complexes as Active Species for the Oxidation of Water and Organic Substrates

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