Ligand-Enabled Gold-Catalyzed Cyanation of Organohalides

被引:5
|
作者
Kumar, Anil [1 ]
Bhattacharya, Nandita [1 ]
Mane, Manoj V. [2 ]
Patil, Nitin T. [1 ]
机构
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal Bypass Rd, Bhopal 462066, India
[2] Jain Deemed Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore 562112, Karnataka, India
关键词
gold; redox catalysis; C(sp(2))-CN coupling; cross-coupling; gold-cyanide; VISIBLE-LIGHT PHOTOREDOX; CROSS-COUPLING REACTIONS; REDUCTIVE ELIMINATION; OXIDATIVE ADDITION; CONVENIENT; COMPLEXES; ARYLATION; CYANIDE; ALKYNES; SALTS;
D O I
10.1002/anie.202412682
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we disclose the first report on gold-catalyzed C(sp(2))-CN cross-coupling reaction by employing a ligand-enabled Au(I)/Au(III) redox catalysis. This transformation utilizes acetone cyanohydrin as a nucleophilic cyanide source to convert simple aryl and alkenyl iodides into the corresponding nitriles. Combined experimental and computational studies highlighted the crucial role of cationic silver salts in activating the stable (P,N)-AuCN complex towards the oxidative addition of aryl iodides to subsequently generate key aryl-Au(III) cyanide complexes.
引用
收藏
页数:7
相关论文
共 50 条
  • [1] Ligand-enabled gold-catalyzed 1,2-heteroarylation of alkenes
    Tathe, Akash G.
    Chintawar, Chetan C.
    Bhoyare, Vivek W.
    Patil, Nitin T.
    CHEMICAL COMMUNICATIONS, 2020, 56 (65) : 9304 - 9307
  • [2] Ligand-Enabled Gold-Catalyzed C(sp2)-O Cross-Coupling Reactions
    Das, Avishek
    Patil, Nitin T.
    ACS CATALYSIS, 2023, 13 (06) : 3847 - 3853
  • [3] Ligand-Enabled Gold-Catalyzed C(sp2)-S Cross-Coupling Reactions
    Tathe, Akash G.
    Patil, Nitin T.
    ORGANIC LETTERS, 2022, 24 (24) : 4459 - 4463
  • [4] Bifunctional phosphine ligand-enabled gold-catalyzed direct cycloisomerization of alkynyl ketones to 2,5-disubstituted furans
    Hu, Xiaojun
    Zhou, Bingwei
    Jin, Hongwei
    Liu, Yunkui
    Zhang, Liming
    CHEMICAL COMMUNICATIONS, 2020, 56 (53) : 7297 - 7300
  • [5] Ligand-Enabled Sustainable Gold Catalysis
    Kumar, Anil
    Patil, Nitin T.
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2022, 10 (21) : 6900 - 6918
  • [6] Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines
    Akram, Manjur O.
    Das, Avishek
    Chakrabarty, Indradweep
    Patil, Nitin T.
    ORGANIC LETTERS, 2019, 21 (19) : 8101 - 8105
  • [7] Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes
    Chen, Hao
    Mondal, Arup
    Wedi, Philipp
    van Gemmeren, Manuel
    ACS CATALYSIS, 2019, 9 (03): : 1979 - 1984
  • [8] Gold-Catalyzed 1,2-Dicarbofunctionalization of Alkynes with Organohalides
    Sancheti, Shashank P.
    Singh, Yukta
    Mane, Manoj V.
    Patil, Nitin T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (42)
  • [9] Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes
    Li, Xingguang
    Wang, Zhixun
    Ma, Xu
    Liu, Pei-nian
    Zhang, Liming
    ORGANIC LETTERS, 2017, 19 (21) : 5744 - 5747
  • [10] Hydrogen bonding-enabled gold catalysis: ligand effects in gold-catalyzed cycloisomerizations in hexafluoroisopropanol (HFIP)
    Tzouras, Nikolaos V.
    Gobbo, Alberto
    Pozsoni, Nestor Bracho
    Chalkidis, Savvas G.
    Bhandary, Subhrajyoti
    Van Hecke, Kristof
    Vougioukalakis, Georgios C.
    Nolan, Steven P.
    CHEMICAL COMMUNICATIONS, 2022, 58 (61) : 8516 - 8519