Copper-Catalyzed Radical Silylarylation of Activated Alkenes: Preparation of β-Silyl Amide-Pharmaceutical Hybrids

被引:7
作者
Chen, Fei [1 ]
Liu, Shi-Yu [1 ]
Li, Xiao [1 ]
Jia, Jia-Lu [1 ]
Li, Yi [1 ]
Lu, Xiao-Lan [1 ]
Jia, Lin [1 ]
Zheng, Yang [1 ]
Yan, Zhongfei [1 ]
Li, Gang [1 ]
Lv, Yunhe [1 ]
Rong, Haojie [2 ]
机构
[1] Anyang Normal Univ, Coll Chem & Chem Engn, Henan Prov Engn Technol Res Ctr Precise Synth Fluo, Henan Prov Key Lab New Optoelect Funct Mat, Anyang 455000, Peoples R China
[2] Xian Modern Chem Res Inst, State Key Lab Fluorine & Nitrogen Chem, Xian 710065, Peoples R China
基金
中国国家自然科学基金;
关键词
silylarylation; alkenes; copper-catalysis; beta-silyl amides; radical cascade reactions; late-stage modification of drug molecules; C-H SILYLATION; ELECTRON-DEFICIENT HETEROARENES; STEREOSELECTIVE-SYNTHESIS; FACILE ACCESS; MIGRATION/DESULFONYLATION; SILANES; ACIDS; DIFUNCTIONALIZATION; HYDROSILYLATION; VINYLSILANES;
D O I
10.1002/adsc.202301434
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Copper-catalyzed silylarylation of N-(arylsulfonyl)acrylamides via a tandem silyl radical addition/1,4-aryl migration/desulfonylation sequence has been developed. This method employs silanes as the precursor of silyl radical and di-tert-butyl peroxide (DTBP) as the initiator. By using this cascade procedure, a series of beta-silyl amide-pharmaceutical hybrids which contain an alpha-all-carbon quaternary stereocenter were facilely synthesized.
引用
收藏
页码:1325 / 1330
页数:6
相关论文
共 96 条
  • [1] Molecular Oxygen Mediated Radical Dicarbofunctionalization of Olefin with Aldehyde
    Biswas, Promita
    Guin, Joyram
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (10) : 5629 - 5638
  • [2] Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides
    Chang, Xi-Hao
    Wang, Zi-Lu
    Zhao, Meng
    Yang, Chao
    Li, Jie-Jun
    Ma, Wei-Wei
    Xu, Yun-He
    [J]. ORGANIC LETTERS, 2020, 22 (04) : 1326 - 1330
  • [3] STRUCTURAL AND CHEMICAL-PROPERTIES OF SILYL RADICALS
    CHATGILIALOGLU, C
    [J]. CHEMICAL REVIEWS, 1995, 95 (05) : 1229 - 1251
  • [4] Chatgilialoglu C., 2004, ORGANOSILANES RADICA
  • [5] Iron-Catalyzed Silylation and Spirocyclization of Biaryl-Ynones: A Radical Cascade Process toward Silylated Spiro[5.5]trienones
    Chen, Fei
    Zheng, Yang
    Yang, Hao
    Yang, Qing-Yun
    Wu, Lu-Yan
    Zhou, Nengneng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (09) : 1537 - 1542
  • [6] Oxoammonium Salt-Mediated Vicinal Oxyazidation of Alkenes with NaN3: Access to β-Aminooxy Azides
    Chen, Fei
    Tang, Yu-Ting
    Li, Xin-Ru
    Duan, Yan-Yan
    Chen, Chao-Xing
    Zheng, Yang
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (22) : 5079 - 5084
  • [7] Cu-Catalyzed Radical Cascade Annulations of Alkyne-Tethered N-Alkoxyamides with Air: Facile Access to Isoxazolidine/1,2-Oxazinane-Fused Isoquinolin-1(2H)-ones
    Chen, Fei
    Lai, Sheng-Qiang
    Zhu, Fei-Fei
    Meng, Qiang
    Jiang, Yu
    Yu, Wei
    Han, Bing
    [J]. ACS CATALYSIS, 2018, 8 (09): : 8925 - 8931
  • [8] Catalytic Silylation of Unactivated C-H Bonds
    Cheng, Chen
    Hartwig, John F.
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 8946 - 8975
  • [9] Organic photoredox catalyzed C-H silylation of quinoxalinones or electron-deficient heteroarenes under ambient air conditions
    Dai, Changhui
    Zhan, Yanling
    Liu, Ping
    Sun, Peipei
    [J]. GREEN CHEMISTRY, 2021, 23 (01) : 314 - 319
  • [10] Palladium-Catalyzed Oxidative Heck-Type Alkylation/Aryl Migration/Desulfonylation between Alkenes with α-Carbonyl Alkyl Bromides
    Fan, Jian-Hong
    Yang, Ji
    Song, Ren-Jie
    Li, Jin-Heng
    [J]. ORGANIC LETTERS, 2015, 17 (04) : 836 - 839