Synthesis of α-Ketoamides via Electrochemical Decarboxylative Acylation of Isocyanides Using α-Ketoacids as an Acyl Source

被引:0
|
作者
Zhao, Yuhan [1 ]
Meng, Xia [1 ]
Cai, Changqun [1 ]
Wang, Lingyun [1 ,2 ]
Gong, Hang [1 ]
机构
[1] Xiangtan Univ, Coll Chem, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environm Friendly Chem & Applicat,Minist, Xiangtan 411105, Peoples R China
[2] Hunan Inst Technol, Sch Mat & Chem Engn, Hengyang 421002, Peoples R China
关键词
alpha-ketoamide; acylation; catalyst-free; decarboxylation; electrochemistry; CATALYZED DOUBLE CARBONYLATION; POTENT THROMBIN INHIBITORS; CATHEPSIN S INHIBITORS; OXOCARBOXYLIC ACIDS; EFFICIENT SYNTHESIS; MINISCI ACYLATION; KETO AMIDES; CHLORIDES; DESIGN; CYCLOTHEONAMIDES;
D O I
10.1002/ajoc.202100748
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A catalyst-, transition metal-, oxidant-free strategy for the synthesis of alpha-ketoamides via an electrochemical decarboxylative acylation of isocyanides at room temperature with carbon dioxide as a sole by-product was developed in this work. This is a simple, rapid and practical strategy under mild conditions for synthesizing highly functionalized alpha-ketoamides with high atom economy.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Metal-free electrochemical synthesis of α-ketoamides via decarboxylative coupling of α-keto acids with isocyanides and water
    Zhao, Feng
    Meng, Na
    Sun, Ting
    Wen, Jiangwei
    Zhao, Xiaohui
    Wei, Wei
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (23): : 6508 - 6514
  • [2] Silver-Catalyzed Decarboxylative Acylation of Isocyanides Accesses to α-Ketoamides with Air as a Sole Oxidant
    Xu, Jia
    Li, Xue
    Chen, Xing-Yu
    He, Yu-Ting
    Lei, Jie
    Chen, Zhong-Zhu
    Xu, Zhi-Gang
    [J]. MOLECULES, 2023, 28 (14):
  • [3] Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids
    Jérémy Merad
    Thomas Maier
    Catarina A. B. Rodrigues
    Nuno Maulide
    [J]. Monatshefte für Chemie - Chemical Monthly, 2017, 148 : 57 - 62
  • [4] Synthesis of γ-pyrones via decarboxylative condensation of β-ketoacids
    Merad, Jeremy
    Maier, Thomas
    Rodrigues, Catarina A. B.
    Maulide, Nuno
    [J]. MONATSHEFTE FUR CHEMIE, 2017, 148 (01): : 57 - 62
  • [5] Electrochemical Multicomponent Synthesis of α-Ketoamides from α-Oxocarboxylic Acids, Isocyanides and Water
    Wu Hongyu
    Yu Xianyong
    Cao Zhong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) : 4712 - 4717
  • [6] Cu(II)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides
    Li, Dengke
    Wang, Min
    Liu, Jie
    Zhao, Qiong
    Wang, Lei
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (35) : 3640 - 3642
  • [7] Visible-Light-Mediated Direct Decarboxylative Acylation of Electron-Deficient Heteroarenes Using α-Ketoacids
    Manna, Sabyasachi
    Prabhu, Kandikere Ramaiah
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09): : 5067 - 5077
  • [8] Selective Synthesis of Amides and α-Ketoamides via Electrochemical Decarboxylation and Dehydration
    Xu, Jiawei
    Huang, Wenxiu
    Li, Mingzhe
    Kang, Chen
    Jiang, Guangbin
    Ji, Fanghua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (15): : 10498 - 10510
  • [9] Efficient Synthesis of α-Ketoamides via 2-Acyl-5-aminooxazoles by Reacting Acyl Chlorides and α-Isocyanoacetamides
    Mossetti, Riccardo
    Pirali, Tracey
    Tron, Gian Cesare
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2010, 12 (04) : 820 - 823
  • [10] Electrochemical synthesis of enaminones via a decarboxylative coupling reaction
    Kong, Xianqiang
    Liu, Yulong
    Lin, Long
    Chen, Qianjin
    Xu, Bo
    [J]. GREEN CHEMISTRY, 2019, 21 (14) : 3796 - 3801