The functionalization of a cascade of C(sp2)-H/C(sp3)-H bonds: synthesis of fused dihydropyrazoles via visible-light photoredox catalysis

被引:38
作者
Cheng, Jian [1 ]
Xu, Pan [1 ]
Li, Weipeng [1 ]
Cheng, Yixiang [1 ]
Zhu, Chengjian [1 ,2 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210023, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
PHOTOCATALYTIC GENERATION; DUAL CATALYSIS; STRATEGY; DIFLUOROALKYLATION; CYCLIZATION; DISCOVERY; ARYLATION; RADICALS; AMINES;
D O I
10.1039/c6cc06410h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The functionalization of a cascade of C(sp(2))-H/C(sp(3))-H bonds in aldehyde hydrazones with simple 2,2-dibromo-1,3-dicarbonyls was achieved via visible-light photoredox catalysis. This method, which involves free radical addition, polar crossover and 6 pi electrocyclic reaction, provides an efficient approach for the synthesis of complex fused dihydropyrazoles and related derivatives with moderate to good yields and excellent regioselectivity under mild reaction conditions.
引用
收藏
页码:11901 / 11904
页数:4
相关论文
共 57 条
  • [1] Bergman J. M., 2006, PCT Int. Appl, Patent No. [WO 2006007491 A1, 2006007491]
  • [2] Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals
    Cai, Shunyou
    Zhao, Xinyang
    Wang, Xinbo
    Liu, Qisong
    Li, Zigang
    Wang, David Zhigang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) : 8050 - 8053
  • [3] Colemam P. J., 2006, PCT Int. Appl, Patent No. [WO 2006023083 A1, 2006023083]
  • [4] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization
    Condie, Allison G.
    Gonzalez-Gomez, Jose C.
    Stephenson, Corey R. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1464 - +
  • [5] Synthesis and SAR of novel conformationally-restricted oxazolidinones possessing Gram-positive and fastidious Gram-negative antibacterial activity. Part 1: Substituted pyrazoles
    Dermyer, Michael R.
    Ding, Qizhu
    Huband, Michael D.
    Jiao, Wenhua
    Kaneko, Takushi
    Khlebnikov, Vladimir
    Kirn, Ji-Young
    Lall, Manjinder S.
    Maiti, Samarendra N.
    Romero, Karina
    Wu, Xiujuan
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (16) : 4694 - 4698
  • [6] Catalytic Asymmetric α-Acylation of Tertiary Amines Mediated by a Dual Catalysis Mode: N-Heterocyclic Carbene and Photoredox Catalysis
    DiRocco, Daniel A.
    Rovis, Tomislav
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) : 8094 - 8097
  • [7] Free radical cyclizations involving nitrogen
    Fallis, AG
    Brinza, IM
    [J]. TETRAHEDRON, 1997, 53 (52) : 17543 - 17594
  • [8] Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light
    Freeman, David B.
    Furst, Laura
    Condie, Allison G.
    Stephenson, Corey R. J.
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 94 - 97
  • [9] Addition of carbon-centered radicals to imines and related compounds
    Friestad, GK
    [J]. TETRAHEDRON, 2001, 57 (26) : 5461 - 5496
  • [10] Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents
    Galliford, Chris V.
    Scheidt, Karl A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8748 - 8758