Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C-C Bond Formation

被引：36
|
作者：
Shimogaki, Mio [1 ]
Fujita, Morifumi [1 ]
Sugimura, Takashi [1 ]
机构：
[1] Univ Hyogo, Grad Sch Mat Sci, 3-2-1 Kohto, Kamigori, Hyogo, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 51期
基金：
日本学术振兴会;
关键词：
cyclization; enantioselectivity; heterocycles; hypervalent compounds; oxidation; ASYMMETRIC-SYNTHESIS; REAGENTS; DIAMINATION; FUNCTIONALIZATION; DIFLUORINATION; REARRANGEMENTS; CATALYSTS; KETONES;
D O I：
10.1002/anie.201609110
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The enantioselective oxyarylation of (E)-6-aryl-1-silyloxylhex-3-ene was achieved using a lactate-based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.
引用
收藏
页码：15797 / 15801
页数：5
相关论文
共 50 条
  • [1] Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C-C Bond Formation
    Shimogaki, Mio
    Fujita, Morifumi
    Sugimura, Takashi
    SYNLETT, 2017, 28 (06) : A59 - A61
  • [2] Metal-Free Oxidative C-C Bond Formation through C-H Bond Functionalization
    Narayan, Rishikesh
    Matcha, Kiran
    Antonchick, Andrey P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (42) : 14678 - 14693
  • [3] Metal-Free Organocatalytic Oxidative Ugi Reaction Promoted by Hypervalent Iodine
    Singh, Karandeep
    Kaur, Amanpreet
    Mithu, Venus Singh
    Sharma, Siddharth
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10): : 5285 - 5293
  • [4] Metal-Free Oxidative Cyclization of Urea-Tethered Alkenes with Hypervalent Iodine
    Cochran, Brian M.
    Michael, Forrest E.
    ORGANIC LETTERS, 2008, 10 (21) : 5039 - 5042
  • [5] Metal-free direct oxidative C-C bond coupling of pyrazolones and quinoxalinones
    Toonchue, Saowanee
    Sumunnee, Ladawan
    Phomphrai, Khamphee
    Yotphan, Sirilata
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (12): : 1928 - 1932
  • [6] Metal-free oxidative cleavage of the C-C bond in α-hydroxy-β-oxophosphonates
    Battula, Satyanarayana
    Kumar, Atul
    Ahmed, Qazi Naveed
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (39) : 9953 - 9956
  • [7] Metal-Free Hypervalent-Iodine-Promoted C3 Difluorination and C2 Oxidation of N-Substituted Indoles
    Sun, Xin
    Zhao, Xiao-Jing
    Wu, Bin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (06) : 690 - 693
  • [8] Metal-Free Oxidative Biaryl Coupling by Hypervalent Iodine Reagents
    Dohi, Toshifumi
    Kita, Yasuyuki
    CURRENT ORGANIC CHEMISTRY, 2016, 20 (05) : 580 - 615
  • [9] Recent Advances in Intramolecular Metal-Free Oxidative C-H Bond Aminations Using Hypervalent Iodine(III) Reagents
    Kandimalla, Satheeshkumar Reddy
    Parvathaneni, Sai Prathima
    Sabitha, Gowravaram
    Reddy, B. V. Subba
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (08) : 1687 - 1714
  • [10] Metal-free oxidative amide formation with N-hydroxysuccinimide and hypervalent iodine reagents
    Yao, Haoyi
    Tang, Yun
    Yamamoto, Kana
    TETRAHEDRON LETTERS, 2012, 53 (38) : 5094 - 5098
12345