Free-Radical Triggered Ordered Domino Reaction: An Approach to C-C Bond Formation via Selective Functionalization of α-Hydroxyl-(sp3)C-H in Fluorinated Alcohols

被引:53
|
作者
Xu, Zhengbao [1 ]
Hang, Zhaojia [1 ]
Liu, Zhong-Quan [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
美国国家科学基金会;
关键词
N-SULFONYL ALDIMINES; H BOND; CASCADE REACTIONS; CARBOXYLIC-ACIDS; NITROGEN-HETEROCYCLES; CATALYZED METHYLATION; ACTIVATED ALKENES; GRIGNARD-REAGENTS; COUPLING REACTION; ALLYLIC ALCOHOLS;
D O I
10.1021/acs.orglett.6b01946
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A free-radical mediated highly ordered radical addition/cydization/(sp(3))C-C(sp(3)) formation domino reaction is developed. Three new C-C bonds are formed one by one in a mixed system. Furthermore, it represents the first example of cascade C-C bond formation via selective functionalization of alpha(-)hydroxyl-C(sp(3))-H in fluorinated alcohols.
引用
收藏
页码:4470 / 4473
页数:4
相关论文
共 50 条
  • [1] Free-Radical Cascade Alkylarylation of Alkenes with Simple Alkanes: Highly Efficient Access to Oxindoles via Selective (sp3)C-H and (sp2)C-H Bond Functionalization
    Li, Zejiang
    Zhang, Ye
    Zhang, Lizhi
    Liu, Zhong-Quan
    ORGANIC LETTERS, 2014, 16 (02) : 382 - 385
  • [2] Advances in C(sp3)-H Bond Functionalization via Radical Processes
    Zhang, Tong
    Wu, Yue-Hua
    Wang, Nai-Xing
    Xing, Yalan
    SYNTHESIS-STUTTGART, 2019, 51 (24): : 4531 - 4548
  • [3] sp3 C-H Bond Functionalization with Ruthenium Catalysts
    Bruneau, Christian
    RUTHENIUM IN CATALYSIS, 2014, 48 : 195 - 236
  • [4] A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp3 C-H bond functionalization
    Li, Zejiang
    Xiao, Yingxia
    Liu, Zhong-Quan
    CHEMICAL COMMUNICATIONS, 2015, 51 (49) : 9969 - 9971
  • [5] β-Cyclodextrin catalysed C-C bond formation via C(sp3)-H functionalization of 2-methyl azaarenes with diones in aqueous medium
    Kumar, Atul
    Shukla, Ratnakar Dutt
    GREEN CHEMISTRY, 2015, 17 (02) : 848 - 851
  • [6] Nickel, Cobalt and Palladium Catalysed C-H Functionalization of Un-Activated C(sp3)-H Bond
    Mishra, Ashish A.
    Subhedar, Dnyaneshwar
    Bhanage, Bhalchandra M.
    CHEMICAL RECORD, 2019, 19 (09) : 1829 - 1857
  • [7] Direct Formation of C-C, C-N, and C-O Bonds in Dihydroquinazolines via Hypervalent Iodine(III)-Mediated sp3 C-H Functionalization
    Carlson, Haley M.
    Smith, Sydney R.
    Mosey, R. Adam
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (02) : 1160 - 1174
  • [8] Selective approach to thioesters and thioethers via sp3 C-H activation of methylarenes
    Feng, J.
    Lu, G. -P.
    Cai, C.
    RSC ADVANCES, 2014, 4 (97) : 54409 - 54415
  • [9] Chelation-Assisted Catalytic C-C, C-Si, and C-Halogen Bond Formation by Substitution via the Cleavage of C(sp2)-H and C(sp3)-H Bonds
    Kakiuchi, Fumitoshi
    Kochi, Takuya
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2015, 73 (11) : 45 - 56
  • [10] Metal-Free Oxidative Functionalization of C(sp3)-H Bond Adjacent to Oxygen and Radical Addition to Olefins
    Zhou, Wei
    Qian, Ping
    Zhao, Jincan
    Fang, Hong
    Han, Jianlin
    Pan, Yi
    ORGANIC LETTERS, 2015, 17 (05) : 1160 - 1163