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
  • [31] Photochromic properties of new benzoindene-fused 2H-chromenes
    Martins, CI
    Coelho, PJ
    Carvalho, LM
    Oliveira-Campos, AMF
    Samat, A
    Guglielmetti, R
    HELVETICA CHIMICA ACTA, 2003, 86 (03) : 570 - 578
  • [32] Furo-fused 2H-chromenes: Synthesis and photochromic properties
    Pozzo, JL
    Samat, A
    Guglielmetti, R
    Lokshin, V
    Minkin, V
    CANADIAN JOURNAL OF CHEMISTRY, 1996, 74 (09) : 1649 - 1659
  • [33] Iron-Catalyzed Rearrangements and Cycloaddition Reactions of 2H-Chromenes
    Luan, Yi
    Sun, Huan
    Schaus, Scott E.
    ORGANIC LETTERS, 2011, 13 (24) : 6480 - 6483
  • [34] An unexpected rearrangement-hydration reaction sequence of 2H-chromenes to dihydrochalcones under catalysis of HAuCl4
    Maiti, Gourhari
    Kayal, Utpal
    Karmakar, Rajiv
    Bhattacharya, Rudraksha N.
    TETRAHEDRON LETTERS, 2012, 53 (47) : 6321 - 6325
  • [35] The Effect of Terminal Bromoalkoxy Substituents on the Photochromism of Functionalized 2H-Chromenes
    Chernikova, Ekaterina Y. Y.
    Perevozchikova, Polina S. S.
    Shepel, Nikolai E. E.
    Fedorova, Olga A. A.
    Fedorov, Yuri V. V.
    CHEMPHOTOCHEM, 2023, 7 (04)
  • [36] Palladium-catalyzed coupling of N-tosylhydrazones and β-bromostyrene derivatives: new approach to 2H-chromenes
    Xia, Yamu
    Xia, Ying
    Zhang, Yan
    Wang, Jianbo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (46) : 9333 - 9336
  • [37] Construction of Diverse and Functionalized 2H-Chromenes by Organocatalytic Multicomponent Reactions
    Cai, Hongyun
    Xia, Likai
    Lee, Yong Rok
    Shim, Jae-Jin
    Kim, Sung Hong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5212 - 5220
  • [38] Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates
    Liu, Fei
    Evans, Todd
    Das, Bhaskar C.
    TETRAHEDRON LETTERS, 2008, 49 (10) : 1578 - 1581
  • [39] Silicon-directed regioselective [2+2] cycloaddition of α-alkoxybenzyne and ketene silyl acetals
    Hosoya, T
    Hamura, T
    Kuriyama, Y
    Miyamoto, M
    Matsumoto, T
    Suzuki, K
    SYNLETT, 2000, (04) : 520 - 522
  • [40] Synthesis of functionalized benzo[f]2H-chromenes and evaluation of their antimicrobial activities
    Irom Harimala Chanu
    Laishram Ronibala Devi
    Nonibala Khumanthem
    N. Irabanta Singh
    Dalip Kumar
    Okram Mukherjee Singh
    Russian Journal of Bioorganic Chemistry, 2017, 43 : 177 - 185
12345