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
  • [21] Cu-Catalyzed Arylcarbocyclization of Alkynes with Diaryliodonium Salts through C-C Bond Formation on Inert C(sp3)-H Bond
    Peng, Jing
    Chen, Chao
    Chen, Junjie
    Su, Xiang
    Xi, Chanjuan
    Chen, Hui
    ORGANIC LETTERS, 2014, 16 (14) : 3776 - 3779
  • [22] A highly site-selective radical sp3 C-H amination of azaheterocycles
    Bentley, Keith W.
    Dummit, Krysta A.
    Van Humbeck, Jeffrey F.
    CHEMICAL SCIENCE, 2018, 9 (30) : 6440 - 6445
  • [23] A Co(II)-catalyzed aerobic intramolecular C-O bond formation via selective (sp3)C-H bond activation: facile access to dihydro-benzoxazinone derivatives
    Shang, Xiao-Jie
    Liu, Zhong-Quan
    TETRAHEDRON LETTERS, 2015, 56 (02) : 482 - 484
  • [24] Recent Advances in Radical-Initiated C(sp3)-H Bond Oxidative Functionalization of Alkyl Nitriles
    Chu, Xue-Qiang
    Ge, Danhua
    Shen, Zhi-Liang
    Loh, Teck-Peng
    ACS CATALYSIS, 2018, 8 (01): : 258 - 271
  • [25] Tuneable access to isoquinolines via a transition-metal-free C(sp3)-C(sp3) bond cleavage rearrangement reaction
    Wang, Jian
    Cai, Panyuan
    He, Yimiao
    Liu, Yuan
    Zhong, Ling
    Ding, Shumin
    Shang, Yongjia
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (14) : 2430 - 2434
  • [26] Synthesis of benzyl esters from the commercially available alcohols catalyzed by TBAI via C(sp3)-H bond functionalization
    Dong, Dao-Qing
    Zhang, Hui
    Wang, Zu-Li
    RSC ADVANCES, 2017, 7 (07): : 3780 - 3782
  • [27] Sc(OTf)3-Catalyzed Domino C-C/C-N Bond Formation of Aziridines with Quinones via Radical Pathway
    Verma, Kshitiz
    Mishra, Manmath
    Maharana, Prabhat Kumar
    Bhattacharyya, Hemanga
    Saha, Sharajit
    Punniyamurthy, Tharmalingam
    ORGANIC LETTERS, 2023, 25 (43) : 7933 - 7938
  • [28] α-Arylchalcogenation of acetone with diaryl dichalcogenide via metal-free oxidative C(sp3)-H bond functionalization
    Yan, Guobing
    Borah, Arun Jyoti
    Wang, Lianggui
    Pan, Zhangjin
    Chen, Shuangshuang
    Shen, Xuqian
    Wu, Xiangmei
    TETRAHEDRON LETTERS, 2015, 56 (29) : 4305 - 4307
  • [29] Enantioselective Gold-Catalyzed Functionalization of Unreactive sp3 C-H Bonds through a Redox-Neutral Domino Reaction
    Zhou, Guanghua
    Liu, Feng
    Zhang, Junliang
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (11) : 3101 - 3104
  • [30] Samarium(III)-Catalyzed C(sp3)-H Bond Activation: Synthesis of Indolizines via C-C and C-N Coupling between 2-Alkylazaarenes and Propargylic Alcohols
    Wang, Xu
    Li, Shen-yan
    Pan, Ying-ming
    Wang, Heng-shan
    Liang, Hong
    Chen, Zhen-feng
    Qin, Xiao-huan
    ORGANIC LETTERS, 2014, 16 (02) : 580 - 583