Synthesis of Carbamoyl Azides from Redox-Active Esters and TMSN 3

被引:1
|
作者
Yuan, Xiaobin [1 ,2 ]
Qu, Yanjie [1 ,2 ]
Li, Yajun [2 ]
Bao, Hongli [2 ]
机构
[1] Fujian Normal Univ, Coll Chem & Mat Sci, Fuzhou 350117, Peoples R China
[2] Chinese Acad Sci, Ctr Excellence Mol Synth, Key Lab Coal Ethylene Glycol & Its Related Technol, State Key Lab Struct Chem, 155 Yangqiao Rd West, Fuzhou 350002, Fujian, Peoples R China
基金
中国国家自然科学基金;
关键词
redox-active esters; iron catalysis; NHP esters; azidation; carbamoyl azides; DECARBOXYLATIVE COUPLING REACTIONS; ONE-POT SYNTHESIS; C-C; SECONDARY ALCOHOLS; KETONES; ACIDS; COMBINATION; CONVERSION; OXIDATION; CURTIUS;
D O I
10.1055/a-2106-5108
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for construction of C-N bonds is reported here. The iron-catalyzed azidation of N-hydroxy phthalimide (NHP) esters provides a convenient approach for the synthesis of carbamoyl azides with good substrate scope and functional group tolerance. Both aryl carbon C(sp(2)) and alkyl carbon C(sp(3)) sources can be used deliver the carbamoyl azides. Mechanistic studies were conducted and a two-stage process was identified.
引用
收藏
页码:464 / 468
页数:5
相关论文
共 50 条
  • [1] A Mild Metal-Free Approach for the Direct Synthesis of Carbamoyl Azides from Carboxylic Acid Redox Active Esters
    Qiu, Yan-Hua
    Zhu, Yuping
    Rao, Ming-Hua
    Huang, Chang-Qi
    Huang, Zi-Ying
    Chen, Zhengwang
    Zhu, Jinbin
    Yu, Daohong
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (12) : 2678 - 2683
  • [2] CuCF3 mediated deoxyfluorination of redox-active esters
    Zou, Zhenlei
    Chang, Wenju
    Zhang, Weigang
    Ni, Shengyang
    Pan, Yi
    Liang, Yong
    Pan, Donghui
    Wang, Yi
    JOURNAL OF FLUORINE CHEMISTRY, 2023, 268
  • [3] Cobalt-catalyzed synthesis of aryl ketones and aldehydes from redox-active esters
    Wang, Lan
    Yu, Jiage
    Duan, Zeqing
    Jin, Jingrong
    Zhang, Yunfei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (33) : 6554 - 6557
  • [4] Photodecarboxylative Amination of Redox-Active Esters with Diazirines
    Maharaj, Vishala
    Chandrachud, Preeti P.
    Che, Wen
    Wojtas, Lukasz
    Lopchuk, Justin M.
    ORGANIC LETTERS, 2021, 23 (22) : 8838 - 8842
  • [5] Decarboxylative amination of redox-active esters using diazirines
    Chandrachud, Preeti
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [6] Decarboxylative amination of redox-active esters using diazirines
    Chandrachud, Preeti
    Lopchuk, Justin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [7] Reliable and Diverse Synthesis of Aryl Azides through Copper-Catalyzed Coupling of Boronic Acids or Esters with TMSN3
    Li, Yu
    Gao, Lian-Xun
    Han, Fu-She
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 7969 - 7972
  • [8] Olefination of aldehydes with alpha-halo redox-active esters
    Liu, Zhengqiang
    Liu, Wenbo H.
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (03) : 885 - 894
  • [9] Synthesis and characterization of redox-active ferric nontronite
    Ilgen, A. G.
    Kukkadapu, R. K.
    Dunphy, D. R.
    Artyushkova, K.
    Cerrato, J. M.
    Kruichak, J. N.
    Janish, M. T.
    Sun, C. J.
    Argo, J. M.
    Washington, R. E.
    CHEMICAL GEOLOGY, 2017, 470 : 1 - 12
  • [10] Synthesis of Redox-Active Photochromic Phenanthrene Derivatives
    Chatir, Elarbi
    Boggio-Pasqua, Martial
    Loiseau, Frederique
    Philouze, Christian
    Royal, Guy
    Cobo, Saioa
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (07)