Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

被引:7
|
作者
He, Tianyu [1 ]
Chen, Dengfeng [1 ]
Qian, Shencheng [1 ]
Zheng, Yu [1 ]
Huang, Shenlin [1 ]
机构
[1] Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Coll Chem Engn, Nanjing 210037, Jiangsu, Peoples R China
基金
中国博士后科学基金;
关键词
SODIUM-NITRITE; KETONES; ACTIVATION; OXIDATION;
D O I
10.1021/acs.orglett.1c02327
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.
引用
收藏
页码:6525 / 6529
页数:5
相关论文
共 50 条
  • [1] Metal-Free, Visible-Light-Induced Selective C-C Bond Cleavage of Cycloalkanones with Molecular Oxygen
    Guo, Li-Na
    Xin, Hong
    Duan, Xin-Hua
    Liu, Le
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (51) : 11690 - 11694
  • [2] Photo- and electrocatalysis for selective C-C bond cleavage
    Zhang, Zehui
    Dai, Wen
    CHEM CATALYSIS, 2021, 1 (07): : 1352 - 1353
  • [3] Electrochemical Oxidation Induced Selective C-C Bond Cleavage
    Shi, Shi-Hui
    Liang, Yujie
    Jiao, Ning
    CHEMICAL REVIEWS, 2021, 121 (01) : 485 - 505
  • [4] A Selective C-C Bond Cleavage Strategy Promoted by Visible Light
    Gallo, Rafael D. C.
    Duarte, Marcelo
    da Silva, Amanda F.
    Okada, Celso Y., Jr.
    Deflon, Victor M.
    Jurberg, Igor D.
    ORGANIC LETTERS, 2021, 23 (22) : 8916 - 8920
  • [5] Selective Dealkenylative Functionalization of Styrenes via C-C Bond Cleavage
    Liu, Jianzhong
    Pan, Jun
    Luo, Xiao
    Qiu, Xu
    Zhang, Cheng
    Jiao, Ning
    RESEARCH, 2020, 2020
  • [6] Carbohydrate ozonation. Selective cleavage of the 2,3 C-C bond in carbohydrates
    Rakovsky, SK
    Sheldon, RA
    Rantwijk, FV
    OXIDATION COMMUNICATIONS, 1996, 19 (04): : 482 - 498
  • [7] C-C Bond Cleavage of Unactivated 2-Acylimidazoles
    Xin, Hai-Long
    Pang, Bo
    Choi, Jeesoo
    Akkad, Walaa
    Morimoto, Hiroyuki
    Ohshima, Takashi
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18): : 11592 - 11606
  • [8] Selective Oxidative Cleavage of the C-C Bond in ?,?-Epoxy Ketone into Carbonyl Compounds
    Jiang, Bing
    Li, Huai-Zhu
    Li, Rui-Jun
    Zhang, Jianye
    Zhang, Yun-Xiao
    ACS OMEGA, 2022, 7 (25): : 21608 - 21614
  • [9] Catalytic selective cleavage of a strong C-C single bond by rhodium in solution
    Liou, SY
    van der Boom, ME
    Milstein, D
    CHEMICAL COMMUNICATIONS, 1998, (06) : 687 - 688
  • [10] Iridium-catalyzed selective C-C bond cleavage of nitriles and ketones
    Terai, H
    Takaya, H
    Murahashi, S
    SYNLETT, 2004, (12) : 2185 - 2187