Photocatalytic C-H Trifluoroethoxylation of (Hetero)arenes

被引:0
|
作者
Chen, Mingxi [1 ]
Ling, Jingjing [1 ]
Cheng, Keguang [1 ,2 ]
Wang, Quande [1 ]
机构
[1] Guangxi Normal Univ, Collaborat Innovat Ctr Guangxi Ethn Med, State Key Lab Chem & Mol Engn Med Resources, Key Lab Chem & Mol Engn Med Resources,Minist Educ, Guilin 541004, Peoples R China
[2] China Pharmaceut Univ, State Key Lab Nat Med, Nanjing 211198, Jiangsu, Peoples R China
关键词
PALLADIUM-CATALYZED 2,2,2-TRIFLUOROETHOXYLATION; BOND FORMATION; ARYL; FACILE; ETHERS; ACCESS; ARENES; ACIDS;
D O I
10.1021/acs.orglett.5c00383
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The trifluoroethoxy group (OCH2CF3) is a valuable motif prevalent in pharmaceuticals and agrichemicals. Herein, we present a simple radical trifluoroethoxylation method that enables nondirected functionalization of C-H bonds of a broad array of substrates, providing access to (hetero)aryl trifluoroethyl ethers. The current protocol tolerates a variety of synthetically and pharmacologically relevant functional groups. Applicability is also demonstrated through the late-stage functionalization of biorelevant molecules and marketing drugs.
引用
收藏
页码:2241 / 2246
页数:6
相关论文
共 50 条
  • [41] Synergistic asymmetric diarylation of tethered alkenes via C-H functionalization of simple (hetero)arenes
    Yao, Jian
    Zhao, Can
    Shao, Lili
    Huo, Xiaohong
    Wang, Xiaoming
    SCIENCE CHINA-CHEMISTRY, 2024, 67 (08) : 2710 - 2718
  • [42] Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ
    Pinacho Crisostomo, Fernando
    Martin, Tomas
    Carrillo, Romen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (08) : 2181 - 2185
  • [43] C-H Alkylations of (Hetero)Arenes by Maleimides and Maleate Esters through Cobalt(III) Catalysis
    Zhang, Zhao
    Han, Shengnan
    Tang, Mengyao
    Ackermann, Lutz
    Li, Jie
    ORGANIC LETTERS, 2017, 19 (12) : 3315 - 3318
  • [44] Cp*CoIII-Catalyzed C-H Activation of (Hetero)arenes: Expanding the Scope of Base-Metal-Catalyzed C-H Functionalizations
    Yoshikai, Naohiko
    CHEMCATCHEM, 2015, 7 (05) : 732 - 734
  • [45] Visible-light-catalyzed C-H arylation of (hetero)arenes via arylselenonium salts
    Wang, Qiyue
    Hao, Xinyu
    Jin, Kun
    Zhang, Rong
    Duan, Chunying
    Li, Yaming
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (21) : 4427 - 4430
  • [46] Metal-free regioselective C-H chalcogenylation of coumarins/(hetero)arenes at ambient temperature
    Song, Zengqiang
    Ding, Chaochao
    Wang, Shaoli
    Dai, Qian
    Sheng, Yaoguang
    Zheng, Zhilong
    Liang, Guang
    CHEMICAL COMMUNICATIONS, 2020, 56 (12) : 1847 - 1850
  • [47] Recent Progress in Iridium-Catalyzed Remote Regioselective C-H Borylation of (Hetero)Arenes
    Zou, Xiaoliang
    Xu, Senmiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (07) : 2610 - 2620
  • [48] Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C-H Activation
    Zhang, Guo-Fu
    Li, Yue
    Xie, Xiao-Qiang
    Ding, Cheng-Rong
    ORGANIC LETTERS, 2017, 19 (05) : 1216 - 1219
  • [49] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [50] Palladium-Catalyzed C-H Trifluoroethoxylation of N-Sulfonylbenzamides
    Yang, Long
    Li, Shangda
    Cai, Lei
    Ding, Yongzheng
    Fu, Lei
    Cai, Zhihua
    Ji, Huafang
    Li, Gang
    ORGANIC LETTERS, 2017, 19 (10) : 2746 - 2749