Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide

Wai Hung Cheung; Wing Ping Yip; Wing Yiu Yu; Chi Ming Che

doi:10.1139/v05-060

Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide

Wai Hung Cheung, Wing Ping Yip, Wing Yiu Yu, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

9 Citations (Scopus)

Abstract

A protocol based on [RuIII(Me3tacn)(CF 3CO2)2(H2O)]CF3CO 2 (1, Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant was developed for oxidation of anisoles to p-benzoquinone monoketals. This reaction can be formally considered as regioselective aromatic C-H oxidation. With 2-methoxyanisole as substrate, 3,4-dimethoxy-4-tert-butoxy-2,5-cyclohexadienone can be obtained in up to 82% yield based on 84% substrate conversion.

Original language	English
Pages (from-to)	521-526
Number of pages	6
Journal	Canadian Journal of Chemistry
Volume	83
Issue number	6-7
DOIs	https://doi.org/10.1139/v05-060
Publication status	Published - 1 Jun 2005
Externally published	Yes

Keywords

Oxidation
Quinones
Ruthenium catalyst
Tert-butyl hydroperoxide

ASJC Scopus subject areas

Catalysis
General Chemistry
Organic Chemistry

More information

10.1139/v05-060

Cite this

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title = "Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide",

abstract = "A protocol based on [RuIII(Me3tacn)(CF 3CO2)2(H2O)]CF3CO 2 (1, Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant was developed for oxidation of anisoles to p-benzoquinone monoketals. This reaction can be formally considered as regioselective aromatic C-H oxidation. With 2-methoxyanisole as substrate, 3,4-dimethoxy-4-tert-butoxy-2,5-cyclohexadienone can be obtained in up to 82% yield based on 84% substrate conversion.",

keywords = "Oxidation, Quinones, Ruthenium catalyst, Tert-butyl hydroperoxide",

author = "Cheung, {Wai Hung} and Yip, {Wing Ping} and Yu, {Wing Yiu} and Che, {Chi Ming}",

year = "2005",

month = jun,

day = "1",

doi = "10.1139/v05-060",

language = "English",

volume = "83",

pages = "521--526",

journal = "Canadian Journal of Chemistry",

issn = "0008-4042",

publisher = "National Research Council of Canada",

number = "6-7",

}

Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide. / Cheung, Wai Hung; Yip, Wing Ping; Yu, Wing Yiu et al.
In: Canadian Journal of Chemistry, Vol. 83, No. 6-7, 01.06.2005, p. 521-526.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide

AU - Cheung, Wai Hung

AU - Yip, Wing Ping

AU - Yu, Wing Yiu

AU - Che, Chi Ming

PY - 2005/6/1

Y1 - 2005/6/1

N2 - A protocol based on [RuIII(Me3tacn)(CF 3CO2)2(H2O)]CF3CO 2 (1, Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant was developed for oxidation of anisoles to p-benzoquinone monoketals. This reaction can be formally considered as regioselective aromatic C-H oxidation. With 2-methoxyanisole as substrate, 3,4-dimethoxy-4-tert-butoxy-2,5-cyclohexadienone can be obtained in up to 82% yield based on 84% substrate conversion.

AB - A protocol based on [RuIII(Me3tacn)(CF 3CO2)2(H2O)]CF3CO 2 (1, Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane) as catalyst and tert-butyl hydroperoxide (TBHP) as oxidant was developed for oxidation of anisoles to p-benzoquinone monoketals. This reaction can be formally considered as regioselective aromatic C-H oxidation. With 2-methoxyanisole as substrate, 3,4-dimethoxy-4-tert-butoxy-2,5-cyclohexadienone can be obtained in up to 82% yield based on 84% substrate conversion.

KW - Oxidation

KW - Quinones

KW - Ruthenium catalyst

KW - Tert-butyl hydroperoxide

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U2 - 10.1139/v05-060

DO - 10.1139/v05-060

M3 - Journal article

SN - 0008-4042

VL - 83

SP - 521

EP - 526

JO - Canadian Journal of Chemistry

JF - Canadian Journal of Chemistry

IS - 6-7

ER -

Oxidation of anisoles to p-benzoquinone monoketals catalyzed by a ruthenium complex of 1,4,7-trimethyl-1,4,7-triazacyclononane with tert-butyl hydroperoxide

Abstract

Keywords

ASJC Scopus subject areas

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