Cobalt-Catalyzed Twofold Direct C(sp2)-C(sp3) Bond Coupling: Regioselective C-3 Alkylation of Coumarins with (Cyclo)alkyl Ethers

被引：37
|
作者：
Dian, Longyang [1 ]
Zhao, Hui [2 ]
Zhang-Negrerie, Daisy [1 ]
Du, Yunfei [1 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China
[2] Shandong Agr Univ, Coll Chem & Mat Sci, Tai An 271018, Shandong, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 15期
基金：
美国国家科学基金会;
关键词：
(cyclo)alkyl ethers; C-H bond functionalization; coumarins; mild conditions; twofold bond coupling; C-H FUNCTIONALIZATION; 4-ARYLCOUMARIN ANALOGS; CROSS-COUPLINGS; 4-SUBSTITUTED COUMARINS; 4-PHENYLCOUMARINS; COMBRETASTATINS; ALKENYLATION; CELLS;
D O I：
10.1002/adsc.201600349
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A cobalt-catalyzed regioselective C-3 alkylation of coumarins was realized under mild reaction conditions, during which a variety of substituted coumarins including those containing sensitive functional groups could smoothly undergo the selective C(sp(2))-C(sp(3)) bond formation with a series of cyclic or straight-chain alkyl ethers.
引用
收藏
页码：2422 / 2426
页数：5
相关论文
共 50 条
  • [31] Preparation of Alkyl Di(p-tolyl)sulfonium Salts and Their Application in Metal-Free C(sp3)-C(sp3) and C(sp3)-C(sp2) Bond Formations
    Higuchi, Kazuhiro
    Yamamoto, Kai
    Nakamura, Shunsuke
    Naruse, Haruka
    Ito, Motoki
    Sugiyama, Shigeo
    ORGANIC LETTERS, 2023, 25 (20) : 3766 - 3771
  • [32] Cobalt-catalyzedreductivealkynylationtoconstructC（sp）-C（sp3）andC（sp）-C（sp2）bonds
    Lei Wan
    Yizhou Tong
    Xi Lu
    Yao Fu
    Chinese Chemical Letters, 2024, 35 (07) : 279 - 284
  • [33] Cobalt(II)-Catalyzed C(sp3)-C(sp3) Coupling for the Direct Stereoselective Synthesis of 2-Deoxy-C-Glycosides from Glycals
    Zeng, Mingjie
    Yu, Changyue
    Wang, Yibing
    Wang, Jingjing
    Wang, Jiang
    Liu, Hong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (22)
  • [34] Cobalt-Catalyzed Oxidative C(sp3)-H Phosphonylation for α-Aminophosphonates via C(sp3)-H/P(O)-H Coupling
    Lin, Binzhou
    Shi, Shanshan
    Lin, Rongcan
    Cui, Yiqun
    Fang, Meijuan
    Tang, Guo
    Zhao, Yufen
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6754 - 6761
  • [35] Cobalt-catalyzed C(sp3)-H bond functionalization to access indole derivatives
    Zhang, He
    Yang, Dandan
    Zhao, Xiao-Fang
    Niu, Jun-Long
    Song, Mao-Ping
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (14) : 3723 - 3729
  • [36] C(sp3)-F, C(sp2)-F and C(sp3)-H bond activation at silicon(II) centers
    Swamy, V. S. V. S. N.
    Parvin, Nasrina
    Raj, K. Vipin
    Vanka, Kumar
    Sen, Sakya S.
    CHEMICAL COMMUNICATIONS, 2017, 53 (71) : 9850 - 9853
  • [37] Palladium Catalysis: Dependence of the Efficiency of C-C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part A: the C(sp2)-C(sp2), C(sp2)-C(sp3) and C(sp3)-C(sp3) Bonds
    Le Bras, Jean
    Muzart, Jacques
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3727 - 3773
  • [38] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Alkyl Grignard Reagents with Polyaromatic Tosylates
    Piontek, Aleksandra
    Szostak, Michal
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (48) : 7271 - 7276
  • [39] Rollover-Assisted C( sp2) -C( sp3) Bond Formation
    Zucca, Antonio
    Maidich, Luca
    Canu, Laura
    Petretto, Giacomo L.
    Stoccoro, Sergio
    Cinellu, Maria Agostina
    Clarkson, Guy J.
    Rourke, Jonathan P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (18) : 5501 - 5510
  • [40] Cobalt-catalysed enantioselective C(sp3)–C(sp3) coupling
    Yan Li
    Wan Nie
    Zhe Chang
    Jia-Wang Wang
    Xi Lu
    Yao Fu
    Nature Catalysis, 2021, 4 : 901 - 911
12345