Copper-Catalyzed Cyanoalkylation and Trifluoromethylthiolation of Styrene Derivatives via a Visible-Light-Promoted Cross-Coupling

被引:1
|
作者
Xu, Xiao-Jing [1 ]
Chi, Zhuo-Min [1 ]
Rui, Rong [1 ]
Zhang, Zhe [1 ]
Li, Hong-Zhe [1 ]
Liu, Xue-Yuan [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
Cyanoalkylation; trifluoromethylthiolation; difunctionalization of styrenes; copper catalysis; visible-light-promoted; CYCLOBUTANONE O-BENZOYLOXIMES; CYCLOKETONE OXIME ESTERS; C-H CYANOALKYLATION; SILVER(I) TRIFLUOROMETHANETHIOLATE; IMINYL RADICALS; CONTAINING PHARMACEUTICALS; SUBSTITUENT CONSTANTS; RING-CLEAVAGE; BOND-CLEAVAGE; ALKENES;
D O I
10.1002/adsc.202400116
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Transition-metal catalyzed difunctionalization of olefins has attracted considerable attention as a method to construct carbon-carbon and carbon-hetero bonds. Herein, the copper-catalyzed three-component radical cross-coupling of oxime esters, styrenes and AgSCF3 through a visible-light-promoted iminyl radical-mediated carbon-carbon bond cleavage strategy has been described. Utilizing low-cost copper salt as both photosensitizers and cross-couplers, this protocol delivers diverse target products, providing a supplementary approach for cyanoalkylation and trifluoromethylthiolation of drug molecules. image
引用
收藏
页码:2607 / 2612
页数:6
相关论文
共 50 条
  • [21] Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes
    Hojoh, Kentaro
    Shido, Yoshinori
    Nagao, Kazunori
    Mori, Seiji
    Ohmiya, Hirohisa
    Sawamura, Masaya
    TETRAHEDRON, 2015, 71 (37) : 6519 - 6533
  • [22] Copper-Catalyzed Cross-Coupling of Allylboronic Acids with α-Diazoketones
    Das, Arindam
    Wang, Dong
    Belhomme, Marie-Charlotte
    Szabo, Kalman J.
    ORGANIC LETTERS, 2015, 17 (19) : 4754 - 4757
  • [23] Recent progress in copper-catalyzed cross-coupling reactions
    Deng, W
    Liu, L
    Guo, QX
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (02) : 150 - 165
  • [24] Copper-Catalyzed Sulfinyl Cross-Coupling Reaction of Sulfinamides
    Kou, Mengting
    Wei, Ziqiang
    Li, Zhen
    Xu, Bin
    ORGANIC LETTERS, 2022, 24 (46) : 8514 - 8519
  • [25] Copper-catalyzed cross-coupling of arenediazonium tetrafluoroborates with polyfluoroarenes
    Zhu, Xingyi
    Li, Feng
    Su, Weike
    TETRAHEDRON LETTERS, 2013, 54 (10) : 1285 - 1289
  • [26] Synthesis of N-Pyridyl Hydroxylamines via Copper-Catalyzed Cross-Coupling
    Torruellas, Carilyn
    Hsu, Fu-Lian
    Walz, Andrew J.
    SYNTHESIS-STUTTGART, 2019, 51 (15): : 2891 - 2896
  • [27] Copper-Catalyzed Oxidative Cross-Coupling of Sulfoximines and Alkynes
    Wang, Long
    Huang, He
    Priebbenow, Daniel L.
    Pan, Fang-Fang
    Bolm, Carsten
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) : 3478 - 3480
  • [28] Photoinduced Copper-Catalyzed Cross-Coupling of Acylsilanes with Heteroarenes via Bimetallic Relay
    Zheng, Long
    Li, Ying-Chao
    Wu, Yichen
    Wang, Peng
    ADVANCED SCIENCE, 2024, 11 (45)
  • [29] Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper-Catalyzed Cross-Coupling Reactions with Elemental Sulfur
    Wu, Peng
    Ward, Jas S.
    Rissanen, Kari
    Bolm, Carsten
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (04) : 522 - 526
  • [30] Visible-Light-Promoted Cross Dehydrogenative/Decarboxylative Coupling Cascades of Glycine Ester Derivatives and β-Keto Acids
    Jiang, Chunhui
    Sha, Xuefei
    Ni, Cheng
    Qin, Wei
    Zhu, Xuejie
    Wang, Shan
    Li, Xuan
    Lu, Hongfei
    JOURNAL OF ORGANIC CHEMISTRY, 2022, : 8744 - 8751