External oxidants in gold-catalyzed cross-coupling reactions

被引:2
|
作者
Koley, Manankar [1 ]
Han, Jianlin [2 ]
Soloshonok, Vadim A. [3 ,4 ]
Mojumder, Subhajit [1 ]
Javahershenas, Ramin [5 ]
Makarem, Ata [6 ]
机构
[1] CSIR Cent Glass & Ceram Res Inst, Kolkata, India
[2] Nanjing Forestry Univ, Coll Chem Engn, Nanjing, Peoples R China
[3] Univ Basque Country, Dept Organ Chem 1, San Sebastian, Spain
[4] Basque Fdn Sci, IKERBASQUE, Bilbao, Spain
[5] Urmia Univ, Fac Chem, Dept Organ Chem, Orumiyeh, Iran
[6] Univ Hamburg, Inst Pharm, Hamburg, Germany
关键词
Cross-coupling; gold catalysis; EBX; PIDA; selectfluor; C-H ALKYNYLATION; TERMINAL ALKYNES; FUNCTIONALIZED HYDRATION; NHC-AUCL/SELECTFLUOR; SELECTIVE SYNTHESIS; OXIDATIVE ADDITION; ARYLBORONIC ACIDS; RHODIUM; ETHYNYLBENZIODOXOLONES; DIFUNCTIONALIZATION;
D O I
10.1080/00958972.2023.2286182
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Au(I)-catalyzed reactions have emerged as an important tool for various organic transformations in the past decade, especially for cross-coupling reactions. However, the exceptionally high reduction potential value of the Au(I)|Au(III) redox couple may act as an obstacle in its development. However, using external mild oxidants in the gold-catalyzed reactions solves this problem effectively. This review gives an overview of different types of oxidants employed in various gold-catalyzed cross-coupling reactions. Such oxidants function via two general mechanistic pathways in which either the oxidation state of the Au(I) atom changes temporarily in the catalytic cycle or it remains intact during the whole process. Therefore, in this article, we also discuss such catalytic reactions from a mechanistic point of view and present the mechanistic proposals given by the authors themselves.
引用
收藏
页码:1 / 48
页数:48
相关论文
共 50 条
  • [1] Gold-Catalyzed Homogeneous Oxidative Cross-Coupling Reactions
    Zhang, Guozhu
    Peng, Yu
    Cui, Li
    Zhang, Liming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (17) : 3112 - 3115
  • [2] Computational Study of Gold-Catalyzed Homo- and Cross-Coupling Reactions
    Nieto Faza, Olalla
    Silva Lopez, Carlos
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (10): : 4929 - 4939
  • [3] Gold-Catalyzed Oxidative Biaryl Cross-Coupling of Organometallics
    Liu, Kai
    Li, Nian
    Ning, Yunyun
    Zhu, Chengjian
    Xie, Jin
    CHEM, 2019, 5 (10): : 2718 - 2730
  • [4] Gold-Catalyzed Cross-Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications
    Nijamudheen, A.
    Datta, Ayan
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (07) : 1442 - 1487
  • [5] Gold-Catalyzed Cross-Coupling and 1,2-Difunctionalization Reactions: A Personal Account
    Ambegave, Shivhar B.
    Patil, Nitin T.
    SYNLETT, 2023, 34 (07) : 698 - 708
  • [6] A computational mechanistic study of gold-catalyzed intermolecular alkene difunctionalization/cross-coupling reactions
    Xing, Yang-Yang
    Chen, De-Zhan
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2024, 1233
  • [7] Mechanistic Investigation into the Gold-Catalyzed Decarboxylative Cross-Coupling of Iodoarenes
    Daley, Ryan A.
    Morrenzin, Aaron S.
    Neufeldt, Sharon R.
    Topczewski, Joseph J.
    ACS CATALYSIS, 2021, 11 (15) : 9578 - 9587
  • [8] Gold-Catalyzed Intramolecular Oxidative Cross-Coupling of Nonactivated Arenes
    Hopkinson, Matthew N.
    Tessier, Arnaud
    Salisbury, Andrew
    Giuffredi, Guy T.
    Combettes, Lorraine E.
    Gee, Antony D.
    Gouverneur, Veronique
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (16) : 4739 - 4743
  • [9] Gold-Catalyzed C-O Cross-Coupling Reactions of Aryl Iodides with Silver Carboxylates
    Chen, Guifang
    Xu, Bo
    ORGANIC LETTERS, 2023, 25 (34) : 6334 - 6339
  • [10] Ligand-Assisted Gold-Catalyzed Cross-Coupling with Aryldiazonium Salts: Redox Gold Catalysis without an External Oxidant
    Cai, Rong
    Lu, Mei
    Aguilera, Ellen Y.
    Xi, Yumeng
    Akhmedov, Novruz G.
    Petersen, Jeffrey L.
    Chen, Hao
    Shi, Xiaodong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8772 - 8776