Iron-Catalyzed, Light-Driven Decarboxylative Alkoxyamination

被引:5
|
作者
Innocent, Milan [1 ]
Tanguy, Clement [1 ]
Gavelle, Sigrid [1 ]
Aubineau, Thomas [1 ]
Guerinot, Amandine [1 ]
机构
[1] CNRS, ESPCI Paris PSL, Mol Macromol Chem & Mat, 10 Rue Vauquelin, F-75005 Paris, France
关键词
iron; photocatalysis; decarboxylation; LMCT; alkoxyamination; C-H ACTIVATION; CARBOXYLIC-ACIDS; CHARGE-TRANSFER; OXIDATION; RADICALS; CLEAVAGE; BIOMASS; LIGAND; TEMPO; OXYAMINATION;
D O I
10.1002/chem.202401252
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iron-catalyzed visible-light driven decarboxylative alkoxyamination is disclosed. In the presence of FeBr2 and TEMPO, a large array of carboxylic acids including marketed drugs and biobased molecules is turned into the corresponding alkoxyamine derivatives. The versatility of the latter offers an entry towards molecular diversity generation from abundant starting materials and catalyst. Overall, this method proposes a unified and general approach for LMCT-based iron-catalyzed decarboxylative functionalization. An iron-catalyzed, visible-light induced decarboxylative alkoxyamination of carboxylic acids with TEMPO is disclosed. In the presence of FeBr2 and TEMPO, a large array of carboxylic acids including marketed drugs and biobased molecules is turned into the corresponding alkoxyamine derivatives. The versatility of the latter offers an entry towards molecular diversity generation from abundant starting materials and catalyst. Overall, this method proposes a unified and general approach for LMCT-based iron-catalyzed decarboxylative functionalization. image
引用
收藏
页数:8
相关论文
共 50 条
  • [1] Iron-Catalyzed, Light-Driven Decarboxylative Oxygenation
    Innocent, Milan
    Lalande, Gabin
    Cam, Francois
    Aubineau, Thomas
    Guerinot, Amandine
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
  • [2] Iron-Catalyzed Asymmetric Decarboxylative Azidation
    Wang, Kaikai
    Li, Yajun
    Li, Xiaoyan
    Li, Daliang
    Bao, Hongli
    ORGANIC LETTERS, 2021, 23 (22) : 8847 - 8851
  • [3] Iron-catalyzed direct decarboxylative azidation
    Haug, Graham C.
    Larionov, Oleg V.
    CHEM CATALYSIS, 2023, 3 (06):
  • [4] Regioselective Iron-Catalyzed Decarboxylative Allylic Etherification
    Trivedi, Rushi
    Tunge, Jon A.
    ORGANIC LETTERS, 2009, 11 (24) : 5650 - 5652
  • [5] Iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light
    Fall, Arona
    Magdei, Mihaela
    Savchuk, Mariia
    Oudeyer, Sylvain
    Beucher, Helene
    Briere, Jean-Francois
    CHEMICAL COMMUNICATIONS, 2024, 60 (49) : 6316 - 6319
  • [6] A General Iron-Catalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids
    Denkler, Luca Mareen
    Shekar, Meghana Aladahalli
    Ngan, Tak Shing Jason
    Wylie, Luke
    Abdullin, Dinar
    Engeser, Marianne
    Schnakenburg, Gregor
    Hett, Tobias
    Pilz, Frank Hendrik
    Kirchner, Barbara
    Schiemann, Olav
    Kielb, Patrycja
    Bunescu, Ala
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (32)
  • [7] Visible-Light-Driven Iron-Catalyzed Decarboxylative C-N Coupling Reaction of Alkyl Carboxylic Acids with NaNO2
    Yang, Shilei
    Wang, Yi
    Xu, Wenyao
    Tian, Xiao
    Bao, Ming
    Yu, Xiaoqiang
    ORGANIC LETTERS, 2023, 25 (49) : 8834 - 8838
  • [8] Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides
    Zhu, Xiaotao
    Ye, Changqing
    Li, Yajun
    Bao, Hongli
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (43) : 10254 - 10258
  • [9] Quinoline Hydroxyalkylations from Iron-Catalyzed, Visible-Light-Driven Decarboxylations
    Rios-Malvaez, Zita G.
    Gonzalez-Rivas, Nelly
    Cuevas-Yanez, Erick
    CATALYSTS, 2024, 14 (12)
  • [10] Light-driven decarboxylative deuteration enabled by a divergently engineered photodecarboxylase
    Jian Xu
    Jiajie Fan
    Yujiao Lou
    Weihua Xu
    Zhiguo Wang
    Danyang Li
    Haonan Zhou
    Xianfu Lin
    Qi Wu
    Nature Communications, 12