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
  • [31] Ruthenium-catalyzed meta/ortho-selective C-H alkylation of azoarenes using alkyl bromides
    Li, Gang
    Ma, Xingxing
    Jia, Chunqi
    Han, Qingqing
    Wang, Ya
    Wang, Junjie
    Yu, Liuyang
    Yang, Suling
    CHEMICAL COMMUNICATIONS, 2017, 53 (07) : 1261 - 1264
  • [32] Site-selective and stereoselective functionalization of non-activated tertiary C-H bonds
    Liao, Kuangbiao
    Pickel, Thomas C.
    Oyarskikh, Vyacheslav B.
    Acsa, John B.
    Usaev, Djamaladdin G. M.
    Davies, Huw M. L.
    NATURE, 2017, 551 (7682) : 609 - 613
  • [33] Functionalization of Non-Activated C-H Bonds in the Synthesis of Vitamin D Metabolites and Analogs
    Moman, Edelmiro
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2014, 14 (21) : 2398 - 2407
  • [34] Alkyl-Branched Fatty Compounds: Hydro-Alkylation of Non-Activated Alkenes With Haloalkanes Mediated by Ethylaluminum Sesquichloride
    Biermann, Ursula
    Metzger, Juergen O.
    EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2018, 120 (01)
  • [35] C(2)H-Alkylation of (Benz)oxazoles with Tertiary Alkyl Chlorides and Bromides under Photoinduced Palladium Catalysis
    Lavrentev, I. V.
    Astakhov, A. V.
    Shepelenko, K. E.
    Chernyshev, V. M.
    DOKLADY CHEMISTRY, 2023, 513 (01) : 327 - 336
  • [36] Photoredox-Catalyzed Oxidative C-H Alkylation of Glycine Derivatives with 4-Alkyl-1,4-dihydropyridines
    Babu, Madala Hari
    Jang, Eunbin
    Jang, Hyesu
    Kim, Sang Kyum
    Sim, Jaehoon
    SYNTHESIS-STUTTGART, 2024, 56 (15): : 2339 - 2346
  • [37] Copper-Mediated Selective Hydroxylation of a Non-activated C-H Bond in Steroids: A DFT Study of Schenecker's Reaction
    Gupta, Puneet
    Diefenbach, Martin
    Holthausen, Max C.
    Foerster, Moritz
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (06) : 1427 - 1435
  • [38] Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides
    Zhou, Wen-Jun
    Cao, Guang-Mei
    Shen, Guo
    Zhu, Xing-Yong
    Gui, Yong-Yuan
    Ye, Jian-Heng
    Sun, Liang
    Liao, Li-Li
    Li, Jing
    Yu, Da-Gang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) : 15683 - 15687
  • [39] Irradiation-Induced Palladium-Catalyzed Direct C-H Alkylation of Heteroarenes with Tertiary and Secondary Alkyl Bromides
    Wang, Guang-Zu
    Shang, Rui
    Fu, Yao
    SYNTHESIS-STUTTGART, 2018, 50 (15): : 2908 - 2914
  • [40] Quantum Dots in Visible-Light Photoredox Catalysis: Reductive Dehalogenations and C-H Arylation Reactions Using Aryl Bromides
    Pal, Anuushka
    Ghosh, Indrajit
    Sapra, Sameer
    Koenig, Burkhard
    CHEMISTRY OF MATERIALS, 2017, 29 (12) : 5225 - 5231
12345