Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system

A method for the selective activation of CH bond of phenol in ortho-position into C-OH bond was developed at room temperature over Cu2+ ions in a two-phase system using marginally water-soluble polar alcohols, acetonitrile and water as solvents and hydrogen peroxide as an oxidant. In a homogeneous...

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Main Authors:	Ke Zheng, Song Shi, Hongchuan Xin, Jin Gao, Zengjian An
Format:	Article
Language:	English
Published:	Elsevier 2021-02-01
Series:	Catalysis Communications
Subjects:	Phenol C-H bond activation Hydroxylation Ortho-position Catechol
Online Access:	http://www.sciencedirect.com/science/article/pii/S1566736720303538

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spelling	doaj-01fb4bd63d5c4221a716dd0e5203daba2021-03-19T07:04:01ZengElsevierCatalysis Communications1873-39052021-02-01150106277Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase systemKe Zheng0Song Shi1Hongchuan Xin2Jin Gao3Zengjian An4Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, PR ChinaState Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, PR ChinaKey Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, PR ChinaState Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, PR China; Corresponding authors.Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, PR China; Corresponding authors.A method for the selective activation of CH bond of phenol in ortho-position into C-OH bond was developed at room temperature over Cu2+ ions in a two-phase system using marginally water-soluble polar alcohols, acetonitrile and water as solvents and hydrogen peroxide as an oxidant. In a homogeneous system, phenol was oxidized to produce catechol and 1,4-hydroquinone with a ratio of 0.77:1.0. The addition of alcohols resulted in a two-phase system, and the ratio of catechol and 1,4-hydroquinone was increased to 4.4:1.0. Compared with a homogeneous system, the selectivity for catechol increased for over 5 times in the two-phase counterpart. This offers an effective hydroxylation method for producing catechol from phenol.http://www.sciencedirect.com/science/article/pii/S1566736720303538PhenolC-H bond activationHydroxylationOrtho-positionCatechol
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Ke Zheng Song Shi Hongchuan Xin Jin Gao Zengjian An
spellingShingle	Ke Zheng Song Shi Hongchuan Xin Jin Gao Zengjian An Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system Catalysis Communications Phenol C-H bond activation Hydroxylation Ortho-position Catechol
author_facet	Ke Zheng Song Shi Hongchuan Xin Jin Gao Zengjian An
author_sort	Ke Zheng
title	Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system
title_short	Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system
title_full	Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system
title_fullStr	Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system
title_full_unstemmed	Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system
title_sort	selective activation of ch bond of phenol in ortho-position into coh bond in a two-phase system
publisher	Elsevier
series	Catalysis Communications
issn	1873-3905
publishDate	2021-02-01
description	A method for the selective activation of CH bond of phenol in ortho-position into C-OH bond was developed at room temperature over Cu2+ ions in a two-phase system using marginally water-soluble polar alcohols, acetonitrile and water as solvents and hydrogen peroxide as an oxidant. In a homogeneous system, phenol was oxidized to produce catechol and 1,4-hydroquinone with a ratio of 0.77:1.0. The addition of alcohols resulted in a two-phase system, and the ratio of catechol and 1,4-hydroquinone was increased to 4.4:1.0. Compared with a homogeneous system, the selectivity for catechol increased for over 5 times in the two-phase counterpart. This offers an effective hydroxylation method for producing catechol from phenol.
topic	Phenol C-H bond activation Hydroxylation Ortho-position Catechol
url	http://www.sciencedirect.com/science/article/pii/S1566736720303538
work_keys_str_mv	AT kezheng selectiveactivationofchbondofphenolinorthopositionintocohbondinatwophasesystem AT songshi selectiveactivationofchbondofphenolinorthopositionintocohbondinatwophasesystem AT hongchuanxin selectiveactivationofchbondofphenolinorthopositionintocohbondinatwophasesystem AT jingao selectiveactivationofchbondofphenolinorthopositionintocohbondinatwophasesystem AT zengjianan selectiveactivationofchbondofphenolinorthopositionintocohbondinatwophasesystem
_version_	1724214465290829824

Selective activation of CH bond of phenol in ortho-position into COH bond in a two-phase system

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