Title:
USE OF NICKEL/KETONE DUAL-CATALYSIS SYSTEM IN CROSS-COUPLING REACTION OF ARYL HALIDE AND SODIUM ARYLSULFINATE
Document Type and Number:
WIPO Patent Application WO/2023/137675
Kind Code:
A1
Abstract:
Disclosed in the present invention is the use of a nickel/ketone dual-catalysis system in a cross-coupling reaction of aryl halide and sodium arylsulfinate. Specifically, in a nitrogen atmosphere, aryl halide, sodium arylsulfinate, nickel bromide trihydrate, 4,4'-di-tert-butyl-2,2'-bipyridine and 2-chloro-thioxanthone are added to a reaction container, which is provided with a stirring device; dimethyl sulfoxide is added thereto; and the mixture is stirred for reaction for 24 hours under room temperature and illumination to obtain a diaryl sulfone compound. In the present invention, the nickel/ketone dual-catalysis system is used without the need for expensive ruthenium or iridium metal complexes and heating conditions, and the reaction conditions are mild. The present invention achieves the efficient preparation of a diaryl sulfone compound; the whole process is green, efficient and easily operated; and the method is a good method for synthesizing a diaryl sulfone compound.
Inventors:
LI HONGXI (CN)
JIANG SHAN (CN)
LI HAIYAN (CN)
JIANG SHAN (CN)
LI HAIYAN (CN)
Application Number:
PCT/CN2022/073056
Publication Date:
July 27, 2023
Filing Date:
January 20, 2022
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07C317/14; C07C43/29; C07C67/31; C07C315/00; C07C315/02
Foreign References:
| CN113717038A | 2021-11-30 | |||
| JPH04120050A | 1992-04-21 | |||
| CN102070498A | 2011-05-25 | |||
| CN101208299A | 2008-06-25 |
Other References:
LIU NAI-WEI, HOFMAN KAMIL, HERBERT ANDRÉ, MANOLIKAKES GEORG: "Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 20, no. 3, 2 February 2018 (2018-02-02), US , pages 760 - 763, XP093079812, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.7b03896
CHAWLA RUCHI, YADAV LAL DHAR S.: "Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 17, no. 19, 15 May 2019 (2019-05-15), pages 4761 - 4766, XP093079817, ISSN: 1477-0520, DOI: 10.1039/C9OB00864K
SUN QIAN, WANG JIN-TANG, ZHANG LI-MIN, YANG MAO-PING: "Photoinduced Electron and Hydrogen Transfer Reactions of Thioxanthone with Amines, Phenols and Alcohols", ACTA PHYSICO-CHIMICA SINICA, vol. 26, no. 9, 1 September 2010 (2010-09-01), pages 2481 - 2488, XP093079825
CHAWLA RUCHI, YADAV LAL DHAR S.: "Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 17, no. 19, 15 May 2019 (2019-05-15), pages 4761 - 4766, XP093079817, ISSN: 1477-0520, DOI: 10.1039/C9OB00864K
SUN QIAN, WANG JIN-TANG, ZHANG LI-MIN, YANG MAO-PING: "Photoinduced Electron and Hydrogen Transfer Reactions of Thioxanthone with Amines, Phenols and Alcohols", ACTA PHYSICO-CHIMICA SINICA, vol. 26, no. 9, 1 September 2010 (2010-09-01), pages 2481 - 2488, XP093079825
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
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