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
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
  • [21] Silyl Radical Mediated Cross-Electrophile Coupling of N-Acyl-imides with Alkyl Bromides under Photoredox/Nickel Dual Catalysis
    Kerackian, Taline
    Reina, Antonio
    Bouyssi, Didier
    Monteiro, Nuno
    Amgoune, Abderrahmane
    ORGANIC LETTERS, 2020, 22 (06) : 2240 - 2245
  • [22] Metal-free C-H borylation of heterocycles by merging photoredox and hydrogen atom transfer catalysis
    Wu, Changfu
    Luo, Shuang
    Liu, Xiaozu
    Liu, Peijun
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (17): : 4785 - 4793
  • [23] Intermolecular C-H Quaternary Alkylation of Aniline Derivatives Induced by Visible-Light Photoredox Catalysis
    Cheng, Jie
    Deng, Xia
    Wang, Guoqiang
    Li, Ying
    Cheng, Xu
    Li, Guigen
    ORGANIC LETTERS, 2016, 18 (18) : 4538 - 4541
  • [24] Site-selective C-H alkylation of myo-inositol via organic photoredox catalysis
    Cao, Haonan
    Guo, Tianyun
    Deng, Xuemei
    Huo, Xing
    Tang, Shouchu
    Liu, Jian
    Wang, Xiaolei
    CHEMICAL COMMUNICATIONS, 2022, 58 (71) : 9934 - 9937
  • [25] Cyclometalated Ruthenium Catalyst Enables Ortho-Selective C-H Alkylation with Secondary Alkyl Bromides
    Wang, Gang-Wei
    Wheatley, Matthew
    Simonetti, Marco
    Cannas, Diego M.
    Larrosa, Igor
    CHEM, 2020, 6 (06): : 1459 - 1468
  • [26] Direct allylic C–H alkylation of enol silyl ethers enabled by photoredox–Brønsted base hybrid catalysis
    Kohsuke Ohmatsu
    Tsubasa Nakashima
    Makoto Sato
    Takashi Ooi
    Nature Communications, 10
  • [27] Photoredox-Mediated Minisci C-H Alkylation Reactions between N-Heteroarenes and Alkyl Iodides with Peroxyacetate as a Radical Relay Initiator
    Wang, Zhen
    Dong, Jianyang
    Hao, Yanan
    Li, Yongqiang
    Liu, Yuxiu
    Song, Hongjian
    Wang, Qingmin
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (24): : 16245 - 16253
  • [28] Regioselective Arene C-H Alkylation Enabled by Organic Photoredox Catalysis (vol 59, pg 7425, 2020)
    Holmberg-Douglas, Natalie
    Onuska, Nicholas P. R.
    Nicewicz, David A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (04)
  • [29] Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis
    Zhang, Xiaheng
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (33) : 11353 - 11356
  • [30] Photoredox-HAT Catalysis for Primary Amine α-C-H Alkylation: Mechanistic Insight with Transient Absorption Spectroscopy
    Sneha, Mahima
    Thornton, Georgia L.
    Lewis-Borrell, Luke
    Ryder, Alison S. H.
    Espley, Samuel G.
    Clark, Ian P.
    Cresswell, Alexander J.
    Grayson, Matthew N.
    Orr-Ewing, Andrew J.
    ACS CATALYSIS, 2023, 13 (12) : 8004 - 8013