Title:
METHOD FOR SYNTHESIZING ARYL PHENOL BY MEANS OF REACTION BETWEEN ARYL HALIDE AND PHENOL COMPOUND UNDER INDUCTION OF VISIBLE LIGHT
Document Type and Number:
WIPO Patent Application WO/2023/142460
Kind Code:
A1
Abstract:
The present invention discloses a method for synthesizing aryl phenol by means of a reaction between an aryl halide and a phenol compound under the induction of visible light, which method comprises: under the protection of an inert gas, stirring and reacting an aryl halide, a phenol compound and cesium carbonate in dimethylsulfoxide (DMSO) at room temperature under the irradiation of visible light so as to obtain a product, namely, an aryl phenol compound. In the present invention, the whole process is green and efficient, and is easy to operate, such that the method is a good method for synthesizing an aryl phenol compound.
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Inventors:
LI HONGXI (CN)
ZHU DALIANG (CN)
LI HAIYAN (CN)
ZHU DALIANG (CN)
LI HAIYAN (CN)
Application Number:
PCT/CN2022/113938
Publication Date:
August 03, 2023
Filing Date:
August 22, 2022
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07C45/68; C07B37/04; C07C49/83; C07C67/343; C07C69/94; C07C253/30; C07C255/57; C07D307/91
Foreign References:
| CN114380675A | 2022-04-22 | |||
| CN114560832A | 2022-05-31 | |||
| CN105967980A | 2016-09-28 |
Other References:
ZHU DA-LIANG, JIANG SHAN, YOUNG DAVID JAMES, WU QI, LI HAI-YAN, LI HONG-XI: "Visible-light-driven C(sp 2 )–H arylation of phenols with arylbromides enabled by electron donor–acceptor excitation", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, vol. 58, no. 22, 15 March 2022 (2022-03-15), UK , pages 3637 - 3640, XP093080235, ISSN: 1359-7345, DOI: 10.1039/D1CC07127K
TEMPESTI TOMAS C., PIERINI ADRIANA B., BAUMGARTNER MARIA T.: "Steric effects of nucleophile-radical coupling reaction. Determination of rate constants for the reaction of aryl radicals with 2-naphthoxide anion", NEW JOURNAL OF CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 33, no. 7, 1 January 2009 (2009-01-01), GB , pages 1523 - 1528, XP093080464, ISSN: 1144-0546, DOI: 10.1039/b820374a
PROTTI STEFANO, MAURIZIO FAGNONI, MARIELLA MELLA ANGELO ALBINI: "Aryl Cations from Aromatic Halides. Photogeneration and Reactivity of 4-Hydroxy(methoxy)phenyl Cation", J. ORG. CHEM., vol. 69, no. 10, 21 April 2004 (2004-04-21), pages 3465 - 3473, XP093080466
LI HAOYU, TANG XINXIN, PANG JIA HAO, WU XIANGYANG, YEOW EDWIN K. L., WU JIE, CHIBA SHUNSUKE: "Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 143, no. 1, 13 January 2021 (2021-01-13), pages 481 - 487, XP093080470, ISSN: 0002-7863, DOI: 10.1021/jacs.0c11968
NAN JIANG, ZUO ZHIJUN, LUO LEI, BAI LU, ZHENG HUAYU, YUAN YINI, LIU JINGJING, LUAN XINJUN, WANG YAOYU: "Ru II -Catalyzed Vinylative Dearomatization of Naphthols via a C(sp 2 )–H Bond Activation Approach", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 135, no. 46, 20 November 2013 (2013-11-20), pages 17306 - 17309, XP093080474, ISSN: 0002-7863, DOI: 10.1021/ja410060e
ZUO ZHIJUN, YANG XIN, LIU JINGJING, NAN JIANG, BAI LU, WANG YAOYU, LUAN XINJUN: "Ru(II)-Catalyzed Oxidative Spiroannulation of 2-Arylphenols with Alkynes via a C–H Activation/Dearomatization Strategy", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 80, no. 6, 20 March 2015 (2015-03-20), pages 3349 - 3356, XP093080479, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b00316
TEMPESTI TOMAS C., PIERINI ADRIANA B., BAUMGARTNER MARIA T.: "Steric effects of nucleophile-radical coupling reaction. Determination of rate constants for the reaction of aryl radicals with 2-naphthoxide anion", NEW JOURNAL OF CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, GB, vol. 33, no. 7, 1 January 2009 (2009-01-01), GB , pages 1523 - 1528, XP093080464, ISSN: 1144-0546, DOI: 10.1039/b820374a
PROTTI STEFANO, MAURIZIO FAGNONI, MARIELLA MELLA ANGELO ALBINI: "Aryl Cations from Aromatic Halides. Photogeneration and Reactivity of 4-Hydroxy(methoxy)phenyl Cation", J. ORG. CHEM., vol. 69, no. 10, 21 April 2004 (2004-04-21), pages 3465 - 3473, XP093080466
LI HAOYU, TANG XINXIN, PANG JIA HAO, WU XIANGYANG, YEOW EDWIN K. L., WU JIE, CHIBA SHUNSUKE: "Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 143, no. 1, 13 January 2021 (2021-01-13), pages 481 - 487, XP093080470, ISSN: 0002-7863, DOI: 10.1021/jacs.0c11968
NAN JIANG, ZUO ZHIJUN, LUO LEI, BAI LU, ZHENG HUAYU, YUAN YINI, LIU JINGJING, LUAN XINJUN, WANG YAOYU: "Ru II -Catalyzed Vinylative Dearomatization of Naphthols via a C(sp 2 )–H Bond Activation Approach", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 135, no. 46, 20 November 2013 (2013-11-20), pages 17306 - 17309, XP093080474, ISSN: 0002-7863, DOI: 10.1021/ja410060e
ZUO ZHIJUN, YANG XIN, LIU JINGJING, NAN JIANG, BAI LU, WANG YAOYU, LUAN XINJUN: "Ru(II)-Catalyzed Oxidative Spiroannulation of 2-Arylphenols with Alkynes via a C–H Activation/Dearomatization Strategy", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 80, no. 6, 20 March 2015 (2015-03-20), pages 3349 - 3356, XP093080479, ISSN: 0022-3263, DOI: 10.1021/acs.joc.5b00316
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
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