Electricity mediated [3+2]-cycloaddition of N-sulfonylcyclopropanes with olefins via N-centered radical intermediates: access to cyclopentane analogs

被引：13
|
作者：
Saha, Debarshi [1 ]
Taily, Irshad Maajid [1 ]
Banerjee, Nakshatra [1 ]
Banerjee, Prabal [1 ]
机构：
[1] Indian Inst Technol IIT, Dept Chem, Lab 406, Rupnagar 140001, Punjab, India
来源：
CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 36期
关键词：
3+2 ANNULATION; CYCLOPROPYLANILINES; DERIVATIVES; GENERATION;
D O I：
10.1039/d2cc00761d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An external oxidant free electrochemical strategy is designed towards the beta-scission of strained C-C bonds in cyclopropylamine. Moreover, the mechanistic studies ascertained that the methodology encompasses the N-center radical (NCRs) route and provides access to di- or tri-substituted cyclopentane analogs.
引用
收藏
页码：5459 / 5462
页数：5
相关论文
共 50 条
  • [31] PhI(OAc)2-Mediated One-Pot Oxidative [3+2] Cycloaddition/ Heterocyclization Reactions of Aldoximes with N-Arylmaleimides: A Facile Access to N-Substituted Pyrrolo-Isoxazoles
    Gairola, Deepti
    Raza, Mohammad Saim
    Roshani, Km
    Peddinti, Rama Krishna
    [J]. CHEMISTRYSELECT, 2023, 8 (26):
  • [32] Asymmetric Construction of 2,3-Dihydroisoxazoles via an Organocatalytic Formal [3+2] Cycloaddition of Enynes with N-Hydroxylamines
    Li, Wenbo
    Yu, Xiuzhao
    Yue, Zhenting
    Zhang, Junliang
    [J]. ORGANIC LETTERS, 2016, 18 (16) : 3972 - 3975
  • [33] Diastereoselective Synthesis of Dispirobarbiturates through Et3N-Catalyzed [3+2] Cycloaddition of Barbiturate-Based Olefins with 3-Isothiocyanato Oxindoles
    Zhao, Hong-Wu
    Tian, Ting
    Li, Bo
    Yang, Zhao
    Pang, Hai-Liang
    Meng, Wei
    Song, Xiu-Qing
    Chen, Xiao-Qin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20): : 10380 - 10385
  • [34] Diastereoselective [3+2] Cycloaddition between Tertiary Amine N-Oxides and Substituted Alkenes to Access 7-Azanorbornanes
    Cocolas, Alexander H.
    Lane, Aiden M.
    Musiak, Benjamin S.
    Chartier, Eric J.
    Bedillion, Derek A.
    Hejnosz, Sarah L.
    Lummis, Paul A.
    Evanseck, Jeffrey D.
    Montgomery, Thomas D.
    [J]. ORGANIC LETTERS, 2024, 26 (31) : 6546 - 6550
  • [35] Silver-catalyzed unstrained C(CO)–alkyl bond scission via [3+2]/retro-[3+2] cycloaddition of ketones with N-isocyanoiminotriphenylphosphorane
    Zikun Wang
    Linxuan Li
    Xueying Zhang
    Xihe Bi
    [J]. Science China(Chemistry) . , 2021, (07) - 1163
  • [36] Silver-catalyzed unstrained C(CO)-alkyl bond scission via [3+2]/retro-[3+2] cycloaddition of ketones with N-isocyanoiminotriphenylphosphorane
    Zikun Wang
    Linxuan Li
    Xueying Zhang
    Xihe Bi
    [J]. Science China Chemistry, 2021, 64 : 1157 - 1163
  • [37] Palladium-catalyzed asymmetric formal [3+2] cycloaddition of α-N-heterocyclic acrylates with vinyl epoxides for construction of isonucleoside analogs
    Huang, Ke-Xin
    Xie, Ming-Sheng
    Wang, Dong-Chao
    Sang, Ji-Wei
    Qu, Gui-Rong
    Guo, Hai-Ming
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (90) : 13550 - 13553
  • [38] Silver-catalyzed unstrained C(CO)–alkyl bond scission via [3+2]/retro-[3+2] cycloaddition of ketones with N-isocyanoiminotriphenylphosphorane
    Zikun Wang
    Linxuan Li
    Xueying Zhang
    Xihe Bi
    [J]. Science China Chemistry, 2021, 64 (07) : 1157 - 1163
  • [39] Silver-catalyzed unstrained C(CO)-alkyl bond scission via [3+2]/retro-[3+2] cycloaddition of ketones with N-isocyanoiminotriphenylphosphorane
    Wang, Zikun
    Li, Linxuan
    Zhang, Xueying
    Bi, Xihe
    [J]. SCIENCE CHINA-CHEMISTRY, 2021, 64 (07) : 1157 - 1163
  • [40] Iodine-catalysed N-centered [1,2]-rearrangement of 3-aminoindazoles with anilines: efficient access to 1,2,3-benzotriazines
    Ren, Jie
    Yan, Xinxin
    Cui, Xiaofan
    Pi, Chao
    Wu, Yangjie
    Cui, Xiuling
    [J]. GREEN CHEMISTRY, 2020, 22 (01) : 265 - 269
12345