Title:
NITROGEN HETEROCYCLIC CARBENE-UREA BIFUNCTIONAL CATALYST AND PREPARATION METHOD THEREFOR
Document Type and Number:
WIPO Patent Application WO/2023/023880
Kind Code:
A1
Abstract:
The present application belongs to the technical field of catalytic materials, and in particular relates to a nitrogen heterocyclic carbene-urea bifunctional catalyst and a preparation method therefor. The general formula of the molecular structure of the metal complex is as shown in formula I in the description, wherein Ar1 and Ar2 in formula I are each independently selected from any one of an aryl, a substituted aryl, a heteroaryl and a substituted heteroaryl. The bifunctionality of the nitrogen heterocyclic carbene-urea is to introduce another active site urea group on the basis of an amino indenol-derived nitrogen heterocyclic carbene skeleton, such that a variety of bifunctional urea-nitrogen heterocyclic carbene catalysts can be formed, and thus same has potential application in the field of organic asymmetric catalysis and can expand organic asymmetric catalytic reactions.
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Inventors:
CHEN JIEAN (CN)
LI EN (CN)
LI EN (CN)
Application Number:
PCT/CN2021/113935
Publication Date:
March 02, 2023
Filing Date:
August 23, 2021
Export Citation:
Assignee:
PINGSHAN TRANSLATIONAL MEDICINE CENTER SHENZHEN BAY LABORATORY (CN)
SHENZHEN BAY LABORATORY (CN)
SHENZHEN BAY LABORATORY (CN)
International Classes:
C07D498/04; B01J31/02
Domestic Patent References:
| WO2007124494A2 | 2007-11-01 |
Foreign References:
| US20110224431A1 | 2011-09-15 | |||
| CN112778328A | 2021-05-11 | |||
| CN113731488A | 2021-12-03 |
Other References:
GUO FANGFANG, CHEN JIEAN, HUANG YONG: "A Bifunctional N-Heterocyclic Carbene as a Noncovalent Organocatalyst for Enantioselective Aza-Michael Addition Reactions", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 11, no. 10, 21 May 2021 (2021-05-21), US , pages 6316 - 6324, XP093038921, ISSN: 2155-5435, DOI: 10.1021/acscatal.1c01908
FAISAL NAWAZ; MEHDI ZAGHOUANI; DAMIEN BONNE; OLIVIER CHUZEL; JEAN RODRIGUEZ; YOANN COQUEREL: "Design, Synthesis, and Organocatalytic Activity of N‐Heterocyclic Carbenes Functionalized with Hydrogen‐Bond Donors in Enantioselective Reactions of Homoenolates", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2013, no. 36, 15 November 2013 (2013-11-15), DE , pages 8253 - 8264, XP072114932, ISSN: 1434-193X, DOI: 10.1002/ejoc.201301366
BRAND JONATHAN, SILES JOSÉ, WASER JÉRÔME: "Synthesis of Chiral Bifunctional (Thio)Urea N-Heterocyclic Carbenes", SYNLETT, GEORG THIEME VERLAG, DE, vol. 2010, no. 06, 1 April 2010 (2010-04-01), DE , pages 881 - 884, XP055931577, ISSN: 0936-5214, DOI: 10.1055/s-0029-1219543
WANG MICHAEL H., COHEN DANIEL T., SCHWAMB C. BENJAMIN, MISHRA RAMA K., SCHEIDT KARL A.: "Enantioselective β-Protonation by a Cooperative Catalysis Strategy", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 137, no. 18, 13 May 2015 (2015-05-13), pages 5891 - 5894, XP093038923, ISSN: 0002-7863, DOI: 10.1021/jacs.5b02887
KUWANO SATORU, HARADA SHINGO, KANG BUBWOONG, ORIEZ RAPHAËL, YAMAOKA YOUSUKE, TAKASU KIYOSEI, YAMADA KEN-ICHI: "Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 135, no. 31, 7 August 2013 (2013-08-07), pages 11485 - 11488, XP093038924, ISSN: 0002-7863, DOI: 10.1021/ja4055838
LIANG, ZHIQIN ET AL.: "Bifunctional N-Heterocyclic Carbene Catalyzed [3+4] Annulation of Enals and Aurones", CHEMISTRY-A EUROPEAN JOURNAL, vol. 21, no. 5, 26 January 2015 (2015-01-26), pages 1868 - 1872, XP071878126, ISSN: 0947-6539, DOI: 10.1002/chem.201405828
FAISAL NAWAZ; MEHDI ZAGHOUANI; DAMIEN BONNE; OLIVIER CHUZEL; JEAN RODRIGUEZ; YOANN COQUEREL: "Design, Synthesis, and Organocatalytic Activity of N‐Heterocyclic Carbenes Functionalized with Hydrogen‐Bond Donors in Enantioselective Reactions of Homoenolates", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2013, no. 36, 15 November 2013 (2013-11-15), DE , pages 8253 - 8264, XP072114932, ISSN: 1434-193X, DOI: 10.1002/ejoc.201301366
BRAND JONATHAN, SILES JOSÉ, WASER JÉRÔME: "Synthesis of Chiral Bifunctional (Thio)Urea N-Heterocyclic Carbenes", SYNLETT, GEORG THIEME VERLAG, DE, vol. 2010, no. 06, 1 April 2010 (2010-04-01), DE , pages 881 - 884, XP055931577, ISSN: 0936-5214, DOI: 10.1055/s-0029-1219543
WANG MICHAEL H., COHEN DANIEL T., SCHWAMB C. BENJAMIN, MISHRA RAMA K., SCHEIDT KARL A.: "Enantioselective β-Protonation by a Cooperative Catalysis Strategy", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 137, no. 18, 13 May 2015 (2015-05-13), pages 5891 - 5894, XP093038923, ISSN: 0002-7863, DOI: 10.1021/jacs.5b02887
KUWANO SATORU, HARADA SHINGO, KANG BUBWOONG, ORIEZ RAPHAËL, YAMAOKA YOUSUKE, TAKASU KIYOSEI, YAMADA KEN-ICHI: "Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 135, no. 31, 7 August 2013 (2013-08-07), pages 11485 - 11488, XP093038924, ISSN: 0002-7863, DOI: 10.1021/ja4055838
LIANG, ZHIQIN ET AL.: "Bifunctional N-Heterocyclic Carbene Catalyzed [3+4] Annulation of Enals and Aurones", CHEMISTRY-A EUROPEAN JOURNAL, vol. 21, no. 5, 26 January 2015 (2015-01-26), pages 1868 - 1872, XP071878126, ISSN: 0947-6539, DOI: 10.1002/chem.201405828
Attorney, Agent or Firm:
SHENZHEN ZHONGYI UNION INTELLECTUAL PROPERTY AGENCY CO., LTD. (CN)
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