Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone

被引：15
|
作者：
Sarma, Manas Jyoti [1 ]
Borah, Arun Jyoti [1 ]
Rajbongshi, Kamal Krishna [1 ]
Phukan, Prodeep [1 ]
机构：
[1] Gauhati Univ, Dept Chem, Gauhati 781014, Assam, India
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 50期
关键词：
C-C cleavage; alpha-Nitroketone; Bromamine-T; Esters; Amide; ACID METHYL-ESTER; ENANTIOSELECTIVE SYNTHESIS; METAL-FREE; ASYMMETRIC AMINOHYDROXYLATION; OXIDATIVE CLEAVAGE; MOLECULAR-OXYGEN; BROMAMINE-T; CARBON; ANTIBACTERIAL; ACTIVATION;
D O I：
10.1016/j.tetlet.2015.11.002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalyst free protocol has been developed for nucleophilic C-sp2 C-sp3 bond cleavage of alpha-nitroketone in the presence of potassium carbonate to create new C-O and C-N bonds. A series of different substituted alpha-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in the presence of alcohols and bromamine-T, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7008 / 7011
页数：4
相关论文
共 50 条
  • [21] New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds
    Sangster, Jack J.
    Marshall, James R.
    Turner, Nicholas J.
    Mangas-Sanchez, Juan
    CHEMBIOCHEM, 2022, 23 (06)
  • [22] Deprotection of benzyl-derived groups via photochemically mesolytic cleavage of C-N and C-O bonds
    Liang, Kangjiang
    Li, Xipan
    Wei, Delian
    Jin, Cuihua
    Liu, Chuanwang
    Xia, Chengfeng
    CHEM, 2023, 9 (02): : 511 - 522
  • [23] C-O Bond Silylation Catalyzed by Iron: A General Method for the Construction of Csp2-Si Bonds
    Zhang, Juan
    Zhang, Yun
    Geng, Shasha
    Chen, Shuo
    Liu, Zhengli
    Zeng, Xiaoqin
    He, Yun
    Feng, Zhang
    ORGANIC LETTERS, 2020, 22 (07) : 2669 - 2674
  • [24] Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation
    Geng, Shasha
    Zhang, Juan
    Chen, Shuo
    Liu, Zhengli
    Zeng, Xiaoqin
    He, Yun
    Feng, Zhang
    ORGANIC LETTERS, 2020, 22 (14) : 5582 - 5588
  • [25] CO2 activation through C-N, C-O and C-C bond formation
    Eftaiha, Ala'a F.
    Qaroush, Abdussalam K.
    Okashah, Ibrahim K.
    Alsoubani, Fatima
    Futter, Jonas
    Troll, Carsten
    Rieger, Bernhard
    Assaf, Khaleel I.
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2020, 22 (03) : 1306 - 1312
  • [26] Advances in Formation of C-X Bonds via Cleavage of C-N Bond of Quaternary Ammonium Salts
    Wang Yiding
    Li Fuhai
    Zeng Qingle
    ACTA CHIMICA SINICA, 2022, 80 (03) : 386 - 394
  • [27] N-Methylpyrrolidin-2-one-Promoted Formation of Functional Esters through C-O Bond Cleavage
    Liu, Jianming
    Wang, Yanyan
    Yue, Yuanyuan
    Liu, Na
    Zhang, Jian
    Zhao, Shufang
    Tang, Qinghu
    Zhuo, Kelei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (18) : 2641 - 2647
  • [28] New advances in the construction of C-N and C-O bonds for organic synthesis
    de Alaniz, Javier Read
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [29] Reactions of a Ru(II) phenyl complex with substrates that possess C-N or C-O multiple bonds: C-C bond formation, N-H bond cleavage, and decarbonylation reactions
    Lee, JP
    Pittard, KA
    DeYonker, NJ
    Cundari, TR
    Gunnoe, TB
    Petersen, JL
    ORGANOMETALLICS, 2006, 25 (06) : 1500 - 1510
  • [30] Ring opening and C-O and C-N bond cleavage by transient reduced thorium species
    Arunachalampillai, Athimoolam
    Crewdson, Patrick
    Korobkov, Ilia
    Gambarotta, Sandro
    ORGANOMETALLICS, 2006, 25 (16) : 3856 - 3866
12345