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
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
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
  • [21] Catalytically oxidative cleavage of lignin C-C bond
    Wang, Feng
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [22] Selective Alkynylallylation of the C-C σ Bond of Cyclopropenes
    Jiang, Zeqi
    Niu, Sheng-Li
    Zeng, Qiang
    Ouyang, Qin
    Chen, Ying-Chun
    Xiao, Qing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (01) : 297 - 303
  • [23] Iron catalyzed ketoalkylation and ketoalkylation/etherification of styrenes initiated by selective C-C bond cleavage
    Suo, Meng-Ting
    Yang, Shuo
    Yang, Jun-Cheng
    Liu, Ze-Yu
    Zhang, Jun-Jie
    Guo, Li-Na
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) : 2414 - 2418
  • [24] Selective C-C bond cleavage of oxidized lignin in an aqueous phase under mild conditions
    Hu, Yuzhen
    Cui, Yanbin
    Zhao, Shuoxiao
    Zhao, Xuelai
    Hu, Xiaohong
    Song, Zhenlong
    Fan, Wei
    Zhang, Qi
    GREEN CHEMISTRY, 2023, 25 (13) : 5150 - 5159
  • [25] Selective aerobic C-C bond cleavage in lignin models and extracts using oxovanadium complexes
    Baker, R. Tom
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [26] Copper catalysts for selective C-C bond cleavage of lignin model compounds and lignin extracts
    Sedai, Baburam
    Diaz-Urrutia, Christian
    Baker, R. Tom
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [27] Zirconocene-Mediated Selective C-C Bond Cleavage of Strained Carbocycles: Scope and Mechanism
    Bruffaerts, Jeffrey
    Vasseur, Alexandre
    Singh, Sukhdev
    Masarwa, Ahmad
    Didier, Dorian
    Oskar, Liron
    Perrin, Lionel
    Eisenstein, Odile
    Marek, Ilan
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 3497 - 3515
  • [28] Selective C-C Bond Cleavage of Methylene-Linked Lignin Models and Kraft Lignin
    Shuai, Li
    Sitison, Jake
    Sadula, Sunitha
    Ding, Junhuan
    Thies, Mark C.
    Saha, Basudeb
    ACS CATALYSIS, 2018, 8 (07): : 6507 - 6512
  • [29] A novel C-C bond cleavage reaction of 2,2′-pyridil in solution
    Ren, R
    Yang, P
    Jin, XL
    CHINESE JOURNAL OF CHEMISTRY, 2001, 19 (11) : 1116 - 1118
  • [30] Selective C-C and C-O bond cleavage strategies for the thermochemical upgrading of (hemi)cellulosic biomass
    Sun, Ruiyan
    Yang, Cui
    Fang, Zheng
    Zhu, Ning
    Zheng, Mingyuan
    Guo, Kai
    Zhang, Tao
    APPLIED CATALYSIS B-ENVIRONMENTAL, 2024, 344
12345