Cobalt(II)-Catalyzed Isocyanide Insertion Reaction with Sulfonyl Azides in Alcohols: Synthesis of Sulfonyl Isoureas

被引：30
|
作者：
Jiang, Tian [1 ,2 ]
Gu, Zheng-Yang [1 ,2 ]
Yin, Ling [1 ,2 ,3 ]
Wang, Shun-Yi [1 ,2 ]
Ji, Shun-Jun [1 ,2 ]
机构：
[1] Soochow Univ, Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China
[3] Jining Univ, Dept Chem & Chem Engn, Qufu 273155, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 15期
基金：
中国国家自然科学基金;
关键词：
TERT-BUTYL ISOCYANIDE; NITROGEN-SOURCE; ORGANIC AZIDES; POLYSUBSTITUTED PYRROLES; CHEMOSELECTIVE SYNTHESIS; NITRENE TRANSFER; DOMINO REACTION; ARYL AZIDES; AMINATION; GUANIDINES;
D O I：
10.1021/acs.joc.7b01127
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Co(II)-catalyzed isocyanide insertion reaction with sulfonyl azides in alcohols to form sulfonyl isoureas via nitrene intermediate has been developed. This protocol provides a new, environmentally friendly, and simple strategy for the synthesis of sulfonyl isourea derivatives by employing a range of substrates under mild conditions.
引用
收藏
页码：7913 / 7919
页数：7
相关论文
共 50 条
  • [1] Cobalt(II)-catalyzed bis-isocyanide insertion reactions with sulfonyl azides via nitrene radicals: chemoselective synthesis of sulfonylamidyl amide and 3-imine indole derivatives
    Gu, Zheng-Yang
    Li, Jing-Hao
    Wang, Shun-Yi
    Ji, Shun-Jun
    CHEMICAL COMMUNICATIONS, 2017, 53 (81) : 11173 - 11176
  • [2] Visible Light Mediated Co-Catalyzed Isocyanide Insertion with Sulfonyl Azide: Synthesis of Sulfonyl Carbamimidic Azide and Sulfonyl Aminotetrazole via Carbodiimide Intermediate
    Ravindra, Sundaresan
    Natarajan, Kannan
    Priya, Vetrivel R. Padma
    Kataria, Ramesh
    Nandi, Ganesh Chandra
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (72)
  • [3] Synthesis of sulfonyl azides
    Katritzky, Alan
    Widyan, Khalid
    Gyanda, Kapil
    SYNTHESIS-STUTTGART, 2008, 8 (08): : 1201 - 1204
  • [4] Sulfonyl azides as precursors in ligand-free palladium-catalyzed synthesis of sulfonyl carbamates and sulfonyl ureas and synthesis of sulfonamides
    Chow, Shiao
    Stevens, Marc
    Odell, Luke
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [5] Sulfonyl Azides as Precursors in Ligand-Free Palladium-Catalyzed Synthesis of Sulfonyl Carbamates and Sulfonyl Ureas and Synthesis of Sulfonamides
    Chow, Shiao Y.
    Stevens, Marc Y.
    Odell, Luke R.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (07): : 2681 - 2691
  • [6] Cobalt(II)-Catalyzed Bis-isocyanides Insertion Reactions with Boric Acids and Sulfonyl Azides via Nitrene Radical Coupling
    Gu, Zheng-Yang
    Zhang, Rong
    Wang, Shun-Yi
    Ji, Shun-Jun
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (11) : 1011 - 1016
  • [7] Ru(II)-catalyzed α-sulfonamidation of cyclic β-ketoesters with sulfonyl azides
    Rao, M. V. Krishna
    Reddy, K. Nagarjuna
    Sridhar, B.
    Reddy, B. V. Subba
    TETRAHEDRON LETTERS, 2019, 60 (41)
  • [8] Diversified synthesis of poly(sulfonyl isourea)s by multicomponent polymerizations of isocyanides, sulfonyl azides, and alcohols/phenols
    Fan, Dongyang
    Chen, Fenggang
    Wang, Dong
    Han, Ting
    Tang, Ben Zhong
    POLYMER CHEMISTRY, 2024, 15 (45) : 4673 - 4681
  • [9] REACTION OF AROMATIC SULFONYL AZIDES WITH DIENES
    ABRAMOVITCH, RA
    ORTIZ, M
    MCMANUS, SP
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02): : 330 - 335
  • [10] ADDITION REACTION OF SULFONYL AZIDES ON ETHOXYACETYLENE
    GRUNANGER, P
    FINZI, PV
    TETRAHEDRON LETTERS, 1963, (26) : 1839 - 1840
12345