Ni-Catalyzed Direct Reductive Amidation via C-O Bond Cleavage

被引:128
|
作者
Correa, Arkaitz [1 ]
Martin, Ruben [1 ,2 ]
机构
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain
基金
欧洲研究理事会;
关键词
UNACTIVATED ALKYL BROMIDES; CROSS-COUPLING REACTIONS; ARYL HALIDES; DIRECT CARBOXYLATION; OXIDATIVE AMIDATION; BENZYL HALIDES; ISOCYANATES; ALDEHYDES; ELECTROPHILES; REACTIVITY;
D O I
10.1021/ja5029793
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel Ni-catalyzed reductive amidation of C(sp(2))-O and C(sp(3))-O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.
引用
收藏
页码:7253 / 7256
页数:4
相关论文
共 50 条
  • [21] Environmentally benign metal triflate-catalyzed reductive cleavage of the C-O bond of acetals to ethers
    Zhang, Yin-Jie
    Dayoub, Wissam
    Chen, Guo-Rong
    Lemaire, Marc
    GREEN CHEMISTRY, 2011, 13 (10) : 2737 - 2742
  • [22] Mechanism of Ni-Catalyzed Selective C-O Bond Activation in Cross-Coupling of Aryl Esters
    Li, Zhe
    Zhang, Song-Lin
    Fu, Yao
    Guo, Qing-Xiang
    Liu, Lei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) : 8815 - 8823
  • [23] Ni-catalyzed mild hydrogenolysis and oxidations of C-O bonds via carbonate redox tags
    Toupalas, Georgios
    Ribadeau-Dumas, Loelie
    Morandi, Bill
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [24] Synthesis of C-Oligosaccharides via Ni-Catalyzed Reductive Hydroglycosylation
    Gulzar, Tayyab
    Liu, Yan-Hua
    Xia, Yu-Nong
    Liu, Wei
    Liu, Pengchao
    Zhu, Dapeng
    Xu, Peng
    Yu, Biao
    ORGANIC LETTERS, 2024, 26 (08) : 1718 - 1722
  • [25] Ligand-controlled cobalt-catalyzed isomerization and reductive C-O bond cleavage of allylic ethers
    Chang, Lijun
    Cai, Cheng
    Chen, Ran
    Chen, Jianhui
    Luo, Yanshu
    Xia, Yuanzhi
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (18): : 4643 - 4648
  • [26] Nickel(II)-Catalyzed Borylation of Alkenyl Methyl Ethers via C-O Bond Cleavage
    Qiu, Xiaodong
    Li, Yangyang
    Zhou, Li
    Chen, Peishan
    Li, Fan
    Zhang, Yanan
    Ling, Yong
    ORGANIC LETTERS, 2020, 22 (16) : 6424 - 6428
  • [27] Enantioselective reductive C-O bond cleavage driven by photoinduced electron transfer
    Wang, Wen-Yao
    Wang, Jing-Jun
    Pan, Jia-Bin
    Xiao, Li-Jun
    Zhou, Qi-Lin
    CHEM, 2024, 10 (12):
  • [28] EFFECTS OF SUBSTITUENTS ON THE REDUCTIVE CLEAVAGE OF THE C-O BOND IN DIPHENYL ETHERS AND DIBENZOFURANES
    SCHMIERS, H
    THETMEYER, E
    STEIN, J
    KLOSE, K
    ZEITSCHRIFT FUR CHEMIE, 1989, 29 (01): : 22 - 23
  • [29] Ni-Catalyzed Stereoselective Arylation of Inert C-O bonds at Low Temperatures
    Cornella, Josep
    Martin, Ruben
    ORGANIC LETTERS, 2013, 15 (24) : 6298 - 6301
  • [30] Borylation of Aryl and Alkenyl Carbamates through Ni-Catalyzed C-O Activation
    Huang, Kun
    Yu, Da-Gang
    Zheng, Shu-Fang
    Wu, Zhen-Hua
    Shi, Zhang-Jie
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (03) : 786 - 791