Visible-Light-Induced External Radical-Triggered Annulation To Access CF2-Containing Benzoxepine Derivatives

被引:58
作者
Xiang, Haoyue [1 ]
Zhao, Qing-Lan [1 ]
Xia, Peng-Ju [1 ]
Xiao, Jun-An [2 ]
Ye, Zhi-Peng [1 ]
Xie, Xiong [1 ]
Sheng, Huan [1 ]
Chen, Xiao-Qing [1 ]
Yang, Hua [1 ]
机构
[1] Cent S Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China
[2] Guangxi Teachers Educ Univ, Coll Chem & Mat Sci, Nanning 530000, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
PHOTOREDOX CATALYSIS; FLUOROALKYLATION REACTIONS; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL EVALUATION; ESTROGEN-RECEPTOR; ALKENES; ACIDS; CYCLIZATION; DIFLUOROALKYLATION; FUNCTIONALIZATION;
D O I
10.1021/acs.orglett.8b00131
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and diversified synthesis of functionalized CF2-containing benzoxepine derivatives via photoredox catalysis was achieved in this work. This novel protocol features broad substrate scope, mild reaction conditions, operational simplicity, easy scale-up, and versatile derivatization, which would facilitate its practical and broad applications in the construction of valuable and synthetically challenging heterocycles.
引用
收藏
页码:1363 / 1366
页数:4
相关论文
共 54 条
  • [1] DIBENZ[B,E]OXEPINALKANOIC ACIDS AS NONSTEROIDAL ANTIINFLAMMATORY AGENTS .2. DIHYDRO-10-OXOFURO AND "THIENO[3,2-C][1]BENZOXEPIN-8-ACETIC ACIDS
    AULTZ, DE
    MCFADDEN, AR
    LASSMAN, HB
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (03) : 456 - 458
  • [2] Photocatalytic fluoroalkylation reactions of organic compounds
    Barata-Vallejo, Sebastian
    Bonesi, Sergio M.
    Postigo, Al
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11153 - 11183
  • [3] Synthesis, biological evaluation, structural-activity relationship, and docking study for a series of benzoxepin-derived estrogen receptor modulators
    Barrett, Irene
    Meegan, Mary J.
    Hughes, Rosario B.
    Carr, Miriam
    Knox, Andrew J. S.
    Artemenko, Natalia
    Golfis, Georgia
    Zisterer, Daniela M.
    Lloyd, David G.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (21) : 9554 - 9573
  • [4] FeCl3-catalyzed synthesis of functionally diverse dibenzo[b,f]oxepines and benzo[b]oxepines via alkyne-aldehyde metathesis
    Bera, Krishnendu
    Jalal, Swapnadeep
    Sarkar, Soumen
    Jana, Umasish
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) : 57 - 61
  • [5] MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID
    BLACKBURN, GM
    ENGLAND, DA
    KOLKMANN, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) : 930 - 932
  • [6] Structure-Based Design of Tricyclic NF-κB Inducing Kinase (NIK) Inhibitors That Have High Selectivity over Phosphoinositide-3-kinase (PI3K)
    Castanedo, Georgette M.
    Blaquiere, Nicole
    Beresini, Maureen
    Bravo, Brandon
    Brightbill, Hans
    Chen, Jacob
    Cui, Hai-Feng
    Eigenbrot, Charles
    Everett, Christine
    Feng, Jianwen
    Godemann, Robert
    Gogol, Emily
    Hymowitz, Sarah
    Johnson, Adam
    Kayagald, Nobuhiko
    Kohli, Pawan Bir
    Knueppel, Kathleen
    Kraemer, Joachim
    Krueger, Susan
    Loke, Pui
    McEwan, Paul
    Montalbetti, Christian
    Roberts, David A.
    Smith, Myron
    Steinbacher, Stefan
    Sujatha-Bhaskar, Swathi
    Takahashi, Ryan
    Wane, Xiaolu
    Wu, Lawren C.
    Zhang, Yamin
    Staben, Steven T.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (02) : 627 - 640
  • [7] Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo[b]oxepine and 2H-Chromene Synthesis
    Chan, Philip Wai Hong
    Teo, Wan Teng
    Koh, Shaun Wei Yong
    Lee, Bo Ra
    Ayers, Benjamin James
    Ma, Dik-Lung
    Leung, Chung-Hang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (20) : 4447 - 4456
  • [8] Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis
    Chatterjee, Tanmay
    Iqbal, Naeem
    You, Youngmin
    Cho, Eun Jin
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) : 2284 - 2294
  • [9] Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond
    Chen, Jia-Rong
    Hu, Xiao-Qiang
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) : 1911 - 1923
  • [10] Photoredox Divergent 1,2-Difunctionalization of Alkenes with gem-Dibromides
    Cheng, Jian
    Cheng, Yixiang
    Xie, Jin
    Zhu, Chengjian
    [J]. ORGANIC LETTERS, 2017, 19 (23) : 6452 - 6455