Copper-Catalyzed Aerobic Spirocyclization of Biaryl-N-H-imines via 1,4-Aminooxygenation of Benzene Rings

被引：48
|
作者：
Tnay, Ya Lin [1 ]
Chen, Cheng [1 ]
Chua, Yi Yuan [1 ]
Zhang, Line [1 ]
Chiba, Shunsuke [1 ]
机构：
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 13期
关键词：
OXIDATIVE AMIDATION; AXIAL CHIRALITY; BOND FORMATION; FUNCTIONALIZATIONS; DEAROMATIZATION; DERIVATIVES; ALKYNES; ACCESS; OXYGEN; SCOPE;
D O I：
10.1021/ol301583y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthetic method of azaspirocyclohexadienones has been developed through copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines prepared by the reaction of biarylcarbonitriles and Grignard reagents.
引用
收藏
页码：3550 / 3553
页数：4
相关论文
共 50 条
  • [1] Copper-Catalyzed Aerobic Aminooxygenation of Cinnamyl N- Alkoxycarbamates via Substrate-Promoted Catalyst Activation
    McNichol, Caitlyn P.
    DeCicco, Ethan M.
    Canfield, Amanda M.
    Carstairs, Daniel P.
    Paradine, Shauna M.
    ACS CATALYSIS, 2023, 13 (10) : 6568 - 6573
  • [2] Copper-catalyzed enantioselective 1,4-addition of alkyl groups to N-sulfonyl imines
    Westmeier, Johannes
    von Zezschwitz, Paultheo
    CHEMICAL COMMUNICATIONS, 2014, 50 (100) : 15897 - 15900
  • [3] Copper-catalyzed 1,3-dipolar cycloaddition of methyleneindolinones and N,N′-cyclic azomethine imines
    Zhang, Di
    Zhang, Da-Ming
    Xu, Guang-Yang
    Sun, Jiang-Tao
    CHINESE CHEMICAL LETTERS, 2015, 26 (03) : 301 - 303
  • [4] Copper-catalyzed 1,3-dipolar cycloaddition of methyleneindolinones and N,N'-cyclic azomethine imines
    Di Zhang
    Da-Ming Zhang
    Guang-Yang Xu
    Jiang-Tao Sun
    Chinese Chemical Letters, 2015, (03) : 301 - 303
  • [5] ONE-POT SYNTHESIS OF 9-SPIROFLUORENES VIA TANDEM COPPER-CATALYZED ARYLATIVE CYCLIZATION AND SPIROCYCLIZATION OF BIARYL-SUBSTITUTED ALKYNYL ALCOHOLS
    Yanada, Reiko
    Okamoto, Noriko
    Sueda, Takuya
    HETEROCYCLES, 2020, 101 (02) : 407 - 416
  • [6] Copper-Catalyzed Benzylic C-H Oxygenation under an Oxygen Atmosphere via N-H Imines as an Intramolecular Directing Group
    Zhang, Line
    Ang, Gim Yean
    Chiba, Shunsuke
    ORGANIC LETTERS, 2011, 13 (07) : 1622 - 1625
  • [7] Copper-Catalyzed Aerobic Cascade Oxidative Coupling/Cyclization for the Construction of 1,4-Dihydropyridine Derivatives
    Zhu, Zhi-Qiang
    Xie, Zong-Bo
    Le, Zhang-Gao
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9449 - 9454
  • [8] Access to drug metabolites via C-H functionalization: copper-catalyzed aerobic oxidation of N,N-dimethylalkylamines in complex pharmaceuticals
    Genovino, Julien
    Sames, Dalibor
    Toure, B. Barry
    TETRAHEDRON LETTERS, 2015, 56 (23) : 3066 - 3069
  • [9] Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage
    Fan, Wenyou
    Yang, Youqing
    Lei, Jianhua
    Jiang, Qijian
    Zhou, Wang
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8782 - 8789
  • [10] Photoinduced Copper-Catalyzed Enantioconvergent Remote Alkynylation via 1,4-Heteroaryl Migration
    Chun, Jianlin
    Li, Yukun
    Xie, Xiaofei
    Guo, Kang
    Zhao, Daoyuan
    Chen, Kang
    Zhu, Yingguang
    ORGANIC LETTERS, 2023, 25 (42) : 7739 - 7744
12345