Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis

被引：21
|
作者：
Haun, Graham [1 ]
Paneque, Alyson N. [1 ]
Almond, David W. [1 ]
Austin, Brooke E. [1 ]
Moura-Letts, Gustavo [1 ]
机构：
[1] Rowan Univ, Dept Chem & Biochem, 201 Mullica Hill Rd, Glassboro, NJ 08028 USA
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 05期
基金：
美国国家科学基金会;
关键词：
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; OPTICALLY-ACTIVE ISOXAZOLIDINES; TRANSITION-METAL-COMPLEXES; TRANSFER RADICAL-ADDITION; ONE-POT SYNTHESIS; PHOTOREDOX CATALYSIS; AROMATIZATION SEQUENCE; ZETEKITOXIN-AB; ALKALOIDS; ALKENES;
D O I：
10.1021/acs.orglett.9b00097
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This effort reports the first redox-neutral visible-light photocatalytic intramolecular dipolar cycloaddition for the diastereoselective synthesis of chromenoisoxazolidines. The authors have found that alkenylphenyl nitrones with a diverse substitution pattern on the aromatic ring and the alkenyl substituent undergo visible-light-promoted cycloadditions in the presence of catalytic amounts of Ru(bpy)(3)Cl-2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.
引用
收藏
页码：1388 / 1392
页数：5
相关论文
共 50 条
  • [41] Visible-Light Photocatalysis of the Ketyl Radical Coupling Reaction
    Xia, Qing
    Dong, Jianyang
    Song, Hongjian
    Wang, Qingmin
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (12) : 2949 - 2961
  • [42] Promoting Visible-Light Photocatalysis with Palladium Species as Cocatalyst
    Li, Xiuzhen
    Zhang, Nan
    Xu, Yi-Jun
    [J]. CHEMCATCHEM, 2015, 7 (14) : 2047 - 2054
  • [43] Synthesis of substituted 2-alkylquinolines by visible-light photoredox catalysis
    Mei, Yousheng
    Liu, Jie
    Wang, Lei
    Li, Pinhua
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (01) : 86 - 92
  • [44] Photocatalysis Meets Magnetism: Designing Magnetically Recoverable Supports for Visible-Light Photocatalysis
    Terra, Julio C. S.
    Desgranges, Ariane
    Monnereau, Cyrille
    Sanchez, Elena H.
    De Toro, Jose A.
    Amara, Zacharias
    Moores, Audrey
    [J]. ACS APPLIED MATERIALS & INTERFACES, 2020, 12 (22) : 24895 - 24904
  • [45] Synthesis of polyaniline modified FeWO4 nanoparticles for superior visible-light photocatalysis
    Liu, Shuangzhi
    Wang, Tianxi
    [J]. MATERIALS LETTERS, 2024, 370
  • [46] Facile Synthesis and Enhanced Visible-Light Photocatalysis of Graphitic Carbon Nitride Composite Semiconductors
    Li, Huiquan
    Liu, Yuxing
    Gao, Xing
    Fu, Cong
    Wang, Xinchen
    [J]. CHEMSUSCHEM, 2015, 8 (07) : 1189 - 1196
  • [47] Direct Synthesis of Polysubstituted Aldehydes via Visible-Light Catalysis
    Wu, Fengjin
    Wang, Leifeng
    Chen, Jiean
    Nicewicz, David A.
    Huang, Yong
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (08) : 2174 - 2178
  • [48] A novel synthesis of P/BiPO4 nanocomposites with enhanced visible-light photocatalysis
    Zong, S.
    Wei, W.
    Cui, H.
    Jiang, Z.
    Lü, X.
    Zhang, M.
    Xie, J.
    [J]. Materials Research Innovations, 2015, 19 (05) : 361 - 367
  • [49] Trifluoroethylation of Alkynes: Synthesis of Allylic-CF3 Compounds by Visible-Light Photocatalysis
    Roh, Geum-bee
    Iqbal, Naeem
    Cho, Eun Jin
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (05) : 459 - 464
  • [50] Visible-Light Mediated Carbamoylation of Nitrones under a Continuous Flow Regime
    Oliveira, Pedro H. R.
    Tordato, Everton A.
    Velez, Jeimy A. C.
    Carneiro, Pablo S.
    Paixao, Marcio W.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (10): : 6407 - 6419
12345