Coupling of 2H-Chromenes with Silyl Ketene Acetals Enabled by Borane Catalysis

被引：4
|
作者：
Liang, Xin-Shen [1 ,2 ]
Li, Rui-Dong [1 ,2 ]
Sun, Wei [1 ,2 ]
Liu, Zhong [1 ,2 ]
Wang, Xiao-Chen [1 ,2 ]
机构：
[1] Nankai Univ, Coll Chem, Frontiers Sci Ctr New Organ Matter, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elemento Organ Chem, Coll Chem, Frontiers Sci Ctr New Organ Matter,Haihe Lab Susta, Tianjin 300071, Peoples R China
来源：
ACS CATALYSIS | 2022年 / 12卷 / 15期
基金：
国家重点研发计划; 中国国家自然科学基金;
关键词：
boron; alkylation; heterocycles; hydrides; homogeneous catalysis; C-H FUNCTIONALIZATION; B(C6F5)(3)-CATALYZED TRANSFER; ACTIVATION; ALPHA; ETHERS; ABSTRACTION; HYDROGENATION; COMBINATION; DIHYDROGEN; CHEMISTRY;
D O I：
10.1021/acscatal.2c02774
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Borane-mediated hydride abstraction has been shown to be a powerful tool for the C(sp(3))-H functionalization of amines, but the same activity with ethers is unknown in the literature. Herein, we report that this activity was observed with 2H-chromenes and the catalytic C(sp(3))-H functionalization reaction based on this activity was established by using silyl ketene acetals as the nucleophiles.
引用
收藏
页码：9153 / 9158
页数：6
相关论文
共 50 条
  • [1] Catalytic Synthesis of 2H-Chromenes
    Majumdar, Nilanjana
    Paul, Nanda D.
    Mandal, Sutanuva
    de Bruin, Bas
    Wulff, William D.
    ACS CATALYSIS, 2015, 5 (04): : 2329 - 2366
  • [2] Metalloradical Approach to 2H-Chromenes
    Paul, Nanda D.
    Mandal, Sutanuva
    Otte, Matthias
    Cui, Xin
    Zhang, X. Peter
    de Bruin, Bas
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) : 1090 - 1096
  • [3] Catalytic Asymmetric Cross-Dehydrogenative Coupling of 2H-Chromenes and Aldehydes
    Pan, Xinhui
    Liu, Xigong
    Sun, Shutao
    Meng, Zhilin
    Liu, Lei
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (12) : 1187 - 1190
  • [4] γ-Lactonizations of 2H-chromenes via cyclopropanation
    Stokes, Sean
    Spears, Ben
    Laseter, Cameron
    Barker, Bobby
    Mead, Keith T.
    TETRAHEDRON LETTERS, 2010, 51 (31) : 4003 - 4006
  • [5] C-C Coupling of Acyclic Nitronates with Silyl Ketene Acetals under Silyl Triflate Catalysis: Reactivity Umpolung of Aliphatic Nitro Compounds
    Smirnov, Vladimir O.
    Khomutova, Yulia A.
    Tartakovsky, Vladimir A.
    Ioffe, Sema L.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (18) : 3377 - 3384
  • [6] CHIRAL (ACYLOXY)BORANE CATALYZED ASYMMETRIC ALDOL TYPE REACTION OF KETENE SILYL ACETALS WITH ALDEHYDES
    FURUTA, K
    MARUYAMA, T
    YAMAMOTO, H
    SYNLETT, 1991, (06) : 439 - 440
  • [7] Coupling Reaction of Enol Derivatives with Silyl Ketene Acetals Catalyzed by Gallium Trihalides
    Nishimoto, Yoshihiro
    Kita, Yuji
    Ueda, Hiroki
    Imaoka, Hiroto
    Chiba, Kouji
    Yasuda, Makoto
    Baba, Akio
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (33) : 11837 - 11845
  • [8] Gallium Tribromide Catalyzed Coupling Reaction of Alkenyl Ethers with Ketene Silyl Acetals
    Nishimoto, Yoshihiro
    Ueda, Hiroki
    Yasuda, Makoto
    Baba, Akio
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) : 8073 - 8076
  • [9] Enantioselective Acylation of Silyl Ketene Acetals through Fluoride Anion-Binding Catalysis
    Birrell, James A.
    Desrosiers, Jean-Nicolas
    Jacobsen, Eric N.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (35) : 13872 - 13875
  • [10] Catalysis by β-Cyclodextrin Hydrate - Synthesis of 2,2-Disubstituted 2H-Chromenes in Aqueous Medium
    Ghatak, Avishek
    Khan, Sagar
    Bhar, Sanjay
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (03) : 435 - 443
12345