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
  • [11] Bifunctional Phosphine Ligand-Enabled Gold(I)-Catalyzed Efficient Synthesis of 1,5-Benzodiazepines
    Zheng, Kanghe
    Zhou, Bingwei
    Jin, Hongwei
    Liu, Yunkui
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (08) : 2520 - 2525
  • [12] Ligand-Enabled NiII-Catalyzed Hydroxylarylation of Alkenes with Molecular Oxygen
    Wang, Dao-Ming
    She, Li-Qin
    Yuan, Hao
    Wu, Yichen
    Tang, Yong
    Wang, Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (35)
  • [13] Ligand-Enabled, Iridium-Catalyzed ortho-Borylation of Fluoroarenes
    Kuleshova, Olena
    Asako, Sobi
    Ilies, Laurean
    ACS CATALYSIS, 2021, 11 (10) : 5968 - 5973
  • [14] Recent advances in ligand-enabled palladium-catalyzed divergent synthesis
    Wang, Yue
    Feng, Jinzan
    Li, Er-Qing
    Jia, Zhenhua
    Loh, Teck-Peng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 22 (01) : 37 - 54
  • [15] Asymmetric Dearomatization of Phenols via Ligand-Enabled Cooperative Gold Catalysis
    Zhang, Yongliang
    Zhao, Ke
    Li, Xinyi
    Quintanilla, Carlos D.
    Zhang, Liming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (38)
  • [16] Ligand-enabled oxidation of gold(i) complexes with o-quinones
    Szaloki, Gyorgy
    Babinot, Julien
    Martin-Diaconescu, Vlad
    Mallet-Ladeira, Sonia
    Garcia-Rodeja, Yago
    Miqueu, Karinne
    Bourissou, Didier
    CHEMICAL SCIENCE, 2022, 13 (35) : 10499 - 10505
  • [17] Ligand-enabled Ni-catalyzed hydroarylation and hydroalkenylation of internal alkenes with organoborons
    Wang, Dao-Ming
    She, Li-Qin
    Wu, Yichen
    Zhu, Chunyin
    Wang, Peng
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [18] Bifunctional diphosphine ligand-enabled cobalt catalyzed bis-alkoxycarbonylation of alkynes
    Luo, Mingxue
    Liu, Zhuchunguang
    Chen, Hua
    Fu, Haiyan
    Li, Ruixiang
    Zheng, Xueli
    JOURNAL OF CATALYSIS, 2024, 433
  • [19] Ligand-enabled Ni-catalyzed hydroarylation and hydroalkenylation of internal alkenes with organoborons
    Dao-Ming Wang
    Li-Qin She
    Yichen Wu
    Chunyin Zhu
    Peng Wang
    Nature Communications, 13
  • [20] Ligand-enabled stereodivergence in nickel-catalyzed regioselective hydroboration of internal allenes
    Yang, Xiaoxu
    Yuan, Chunchen
    Ge, Shaozhong
    CHEM, 2023, 9 (01): : 198 - 215