Photoredox Catalysis for Silyl-Mediated C-H Alkylation of Heterocycles with Non-Activated Alkyl Bromides

被引：23
|
作者：
Perkins, James J. [1 ]
Schubert, Jeffrey W. [1 ]
Streckfuss, Eric C. [1 ]
Balsells, Jaume [2 ]
ElMarrouni, Abdellatif [1 ]
机构：
[1] Merck & Co Inc, MRL, Dept Discovery Chem, 770 Sumneytown Pike, West Point, PA 19486 USA
[2] Janssen Res & Dev LLC, Spring House, PA 19477 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 10期
关键词：
Alkylation; Minisci reaction; Photoredox catalysis; Synthetic methods; Visible light; LATE-STAGE FUNCTIONALIZATION; MEDICINAL CHEMISTS TOOLBOX; HETEROARENES; SUBSTITUTIONS; ALCOHOLS;
D O I：
10.1002/ejoc.201900611
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of a Minisci reaction of electron-deficient heteroarenes with non-activated alkyl bromides under visible-light photoredox catalysis is disclosed. Optimization of the reaction led to identification of mild, general, and practical reaction conditions compatible with sensitive functional groups. The scope of this transformation allowed late-stage functionalization of pharmaceutical products containing electron-deficient heteroarenes in a parallel fashion.
引用
收藏
页码：1515 / 1522
页数：8
相关论文
共 50 条
  • [1] Silyl-mediated photoredox-catalyzed Giese reaction: addition of non-activated alkyl bromides
    ElMarrouni, Abdellatif
    Ritts, Casey B.
    Balsells, Jaume
    CHEMICAL SCIENCE, 2018, 9 (32) : 6639 - 6646
  • [2] Aliphatic C-H alkylation via photoredox catalysis
    Morton, Carla
    Choi, Gilbert
    Zhu, Qilei
    Knowles, Robert
    Alexanian, Erik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [3] Silyl-mediated photoredox-catalyzed radical-radical cross-coupling reaction of alkyl bromides and ketoesters
    Jiang, Hao-Luo
    Yang, Yu-Hao
    Zhao, Ya-Nan
    He, Yan-Hong
    Guan, Zhi
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23): : 6611 - 6616
  • [4] C-H Alkylation of Heterocycles via Light-Mediated Palladium Catalysis
    Senapati, Sudip
    Kumar Hota, Sudhir
    Kloene, Lennard
    Empel, Claire
    Murarka, Sandip
    Koenigs, Rene M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (08)
  • [5] Mechanochemical Magnesium-Mediated Minisci C-H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides
    Wu, Chongyang
    Ying, Tao
    Yang, Xinjie
    Su, Weike
    Dushkin, Alexandr V.
    Yu, Jingbo
    ORGANIC LETTERS, 2021, 23 (16) : 6423 - 6428
  • [6] Direct C-H difluoromethylation of heterocycles via organic photoredox catalysis
    Zhang, Wei
    Xiang, Xin-Xin
    Chen, Junyi
    Yang, Chen
    Pan, Yu-Liang
    Cheng, Jin-Pei
    Meng, Qingbin
    Li, Xin
    NATURE COMMUNICATIONS, 2020, 11 (01)
  • [7] Regioselective Arene C-H Alkylation Enabled by Organic Photoredox Catalysis
    Holmberg-Douglas, Natalie
    Onuska, Nicholas P. R.
    Nicewicz, David A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (19) : 7425 - 7429
  • [8] Direct C-H Alkylation of Benzothiadiazoles via Organic Photoredox Catalysis
    Xu, Guiqing
    Lv, Jiayuan
    Ding, Qingjie
    Ma, Chunhua
    Jiang, Yuqin
    Yu, Bing
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (04): : 2777 - 2781
  • [9] Direct allylic C-H alkylation of enol silyl ethers enabled by photoredox-Bronsted base hybrid catalysis
    Ohmatsu, Kohsuke
    Nakashima, Tsubasa
    Sato, Makoto
    Ooi, Takashi
    NATURE COMMUNICATIONS, 2019, 10 (1)
  • [10] Photoredox/rhodium catalysis in C-H activation for the synthesis of nitrogen containing heterocycles
    Kim, Hyun Jin
    Fabry, David C.
    Mader, Steffen
    Rueping, Magnus
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (14) : 2319 - 2323
12345