Palladium-Catalyzed Electrooxidative Hydrofluorination of Aryl-Substituted Alkenes with a Nucleophilic Fluorine Source

被引:10
|
作者
Mandal, Anup [1 ]
Jang, Jieun [1 ]
Yang, Baeho [1 ]
Kim, Hyunwoo [2 ]
Shin, Kwangmin [1 ]
机构
[1] Sungkyunkwan Univ, Dept Chem, Suwon 16419, South Korea
[2] Pohang Univ Sci & Technol POSTECH, Dept Chem, Pohang 37673, South Korea
基金
新加坡国家研究基金会;
关键词
C-H FLUORINATION; ELECTROCHEMICAL FLUORINATION;
D O I
10.1021/acs.orglett.2c04045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report an electrocatalytic hydrofluorination of aryl-substituted alkenes with a nucleophilic fluorine source. The merger of palladium catalysis with electrooxidation enables the transformation of various substrates ranging from styrenes to more challenging alpha,beta-unsaturated carbonyl derivatives to the corresponding benzylic fluorides. This method can also be applied to the late-stage modification of pharmaceutical derivatives. Mechanistic studies suggest that the generation of a high-valent palladium intermediate via anodic oxidation is the crucial step in this electrocatalytic hydrofluorination.
引用
收藏
页码:195 / 199
页数:5
相关论文
共 50 条
  • [1] Palladium-Catalyzed Formal Hydroalkylation of Aryl-Substituted Alkynes with Hydrazones
    Yu, Lin
    Lv, Leiyang
    Qiu, Zihang
    Chen, Zhangpei
    Tan, Ze
    Liang, Yu-Feng
    Li, Chao-Jun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (33) : 14009 - 14013
  • [2] Palladium-catalyzed ring enlargement of aryl-substituted methylenecyclopropanes to cyclobutenes
    Shi, Min
    Liu, Le-Ping
    Tang, Jie
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (23) : 7430 - 7431
  • [3] Palladium-catalyzed synthesis of aryl-substituted polyamine compounds from aryl halides.
    Beletskaya, IP
    Bessmertnykh, AG
    Guilard, R
    TETRAHEDRON LETTERS, 1997, 38 (13) : 2287 - 2290
  • [4] Palladium-catalyzed heteroannulation of cyclic alkenes by functionally substituted aryl iodides
    Emrich, DE
    Larock, RC
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) : 3756 - 3766
  • [5] Palladium-catalyzed isomerization of aryl-substituted epoxides: A selective synthesis of substituted benzylic aldehydes and ketones
    Kulasegaram, S
    Kulawiec, RJ
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19): : 6547 - 6561
  • [6] Palladium-Catalyzed Intramolecular [4+2] Cycloadition Reactions of Aryl-Substituted Diynes
    Wu, Yuqin
    Yang, Yong
    Li, Lidong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (11) : 2333 - 2339
  • [7] A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide
    Tjutrins, Jevgenijs
    Arndtsen, Bruce A.
    CHEMICAL SCIENCE, 2017, 8 (02) : 1002 - 1007
  • [8] Enantioselective Palladium-Catalyzed Hydrofluorination of Alkenylarenes
    Yin, Xuemei
    Chen, Bin
    Qiu, Feng
    Wang, Xihong
    Liao, Yang
    Wang, Min
    Lei, Xinxiang
    Liao, Jian
    ACS CATALYSIS, 2020, 10 (03) : 1954 - 1960
  • [9] Palladium-catalyzed coupling of aryl bromides with aryl boranes, alkenes, and alkynes to produce byaryls, substituted alkenes, and alkynes.
    De, DBY
    Krogstad, DJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U197 - U197
  • [10] Palladium-catalyzed annulation of aryl heterocycles with strained alkenes
    Hulcoop, David G.
    Lautens, Mark
    ORGANIC LETTERS, 2007, 9 (09) : 1761 - 1764