Facile access to ?-hydroxyl ketones via a cobalt-catalyzed ring-opening/hydroxylation cascade of cyclopropanols

被引:6
作者
Zhai, Shengxian [1 ]
Qiu, Shuxian [2 ]
Yang, Shuangtao [1 ]
Gao, Xingyuan [2 ]
Feng, Xinyu [1 ]
Yun, Chenzhe [1 ]
Han, Ning [1 ]
Niu, Yongsheng [1 ]
Wang, Jing [1 ]
Zhai, Hongbin [3 ,4 ,5 ,6 ]
机构
[1] Anyang Inst Technol, Coll Chem & Environm Engn, Anyang 455000, Peoples R China
[2] Guangdong Univ Educ, Engn Technol Dev Ctr Adv Mat & Energy Saving Emiss, Guangzhou 510303, Peoples R China
[3] Peking Univ, State Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[4] Peking Univ, Key Lab Chem Genom, Shenzhen Engn Lab Nano Drug Slow Release, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[5] Shenzhen Bay Lab, Shenzhen 518055, Peoples R China
[6] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
Cobalt catalysis; Ring-opening; Cyclopropanol; -Hydroxy ketone; Cascade reaction; C BOND-CLEAVAGE; EFFICIENT SYNTHESIS; H ACTIVATION; VINYL AZIDES; BETA; STRATEGY; FUNCTIONALIZATION; CHEMISTRY; TRIFLUOROMETHYLATION; FLUORINATION;
D O I
10.1016/j.cclet.2022.06.080
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A cobalt-catalyzed ring-opening/hydroxylation cascade of highly strained cyclopropanols has been developed for the first time. The reaction was conducted under open-air atmosphere to afford a broad series of structurally diverse /3-hydroxy ketones in moderate to good yields with high regioselectivity. The protocol features mild reaction conditions, simple operation, high-functional-group tolerance, facile scalability, and heterocycle compatibility.(c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
引用
收藏
页数:4
相关论文
共 50 条
  • [31] Intermolecular Oxidative Radical Addition to Aromatic Aldehydes: Direct Access to 1,4-and 1,5-Diketones via Silver-Catalyzed Ring-Opening Acylation of Cyclopropanols and Cyclobutanols
    Che, Chao
    Qian, Zhaosheng
    Wu, Mingchang
    Zhao, Ying
    Zhu, Gangguo
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) : 5665 - 5673
  • [32] Nickel-Catalyzed Ring-Opening Hydroacylation of Methylenecyclopropanes: Synthesis of γ,δ-Unsaturated Ketones from Aldehydes
    Taniguchi, Hiroki
    Ohmura, Toshimichi
    Suginome, Michinori
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (32) : 11298 - +
  • [33] [5+2] Cycloaddition of 2-(2-Aminoethyl)oxiranes with Alkynes via Epoxide Ring-Opening: A Facile Access to Azepines
    Hu, Chao
    Song, Ren-Jie
    Hu, Ming
    Yang, Yuan
    Li, Jin-Heng
    Luo, Shenglian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) : 10423 - 10426
  • [34] Facile Synthesis of Trisubstituted Carbazoles by Acid-Catalyzed Ring-Opening Annulation of 2-Amidodihydrofurans with Indoles
    Zhao, Jingjing
    Li, Pan
    Xia, Chungu
    Li, Fuwei
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (46) : 16383 - 16386
  • [35] Copper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes
    Che, Chao
    Huang, Qianwen
    Zheng, Hanliang
    Zhu, Gangguo
    CHEMICAL SCIENCE, 2016, 7 (07) : 4134 - 4139
  • [36] Acid-Catalyzed Cascade Ring-Opening and Addition Reactions of Arylvinylcyclopropenes with α,β-Unsaturated Substrates, Scope and Limitations
    Zhu, Zhi-Bin
    Shi, Min
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) : 2481 - 2485
  • [37] Organotin-catalyzed synthesis of hydroxyalkylamides from lactones via a ring-opening process
    Liang, Xiayu
    Yu, Peng
    Fu, Chen
    Shen, Yongcun
    TETRAHEDRON LETTERS, 2021, 66
  • [38] Access to Divergent Fluorinated Enynes and Arenes via Palladium-Catalyzed Ring-Opening Alkynylation of gem-Difluorinated Cyclopropanes
    Ahmed, Ebrahim-Alkhalil M. A.
    Suliman, Ayman M. Y.
    Gong, Tian-Jun
    Fu, Yao
    ORGANIC LETTERS, 2020, 22 (04) : 1414 - 1419
  • [39] Cobalt-catalyzed highly diastereoselective [3+2] carboannulation reactions: facile access to substituted indane derivatives
    Dey, Arnab
    Singh, Anurag
    Volla, Chandra M. R.
    CHEMICAL COMMUNICATIONS, 2022, 58 (09) : 1386 - 1389
  • [40] Rhodium(III)-Catalyzed Mild Alkylation of (Hetero)Arenes with Cyclopropanols via C-H Activation and Ring Opening
    Zhou, Xukai
    Yu, Songjie
    Qi, Zisong
    Kong, Lingheng
    Li, Xingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11) : 4869 - 4875