Transition-Metal-Free Dehydrosilylative Difluoroamidation of Tetrahydroisoquinolines under Mild Conditions

被引:42
|
作者
Chen, Qiao [1 ]
Zhou, Jiawei [1 ]
Wang, Yanan [1 ]
Wang, Chao [1 ]
Liu, Xihong [1 ]
Xu, Zhaoqing [1 ]
Lin, Li [1 ]
Wang, Rui [1 ]
机构
[1] Lanzhou Univ, Sch Basic Med Sci, Key Lab Preclin Study New Drugs Gansu Prov, Lanzhou 730000, Peoples R China
关键词
H BOND FUNCTIONALIZATION; CARBON-HYDROGEN BONDS; TERTIARY-AMINES; NITROGEN ATOM; MEDICINAL CHEMISTRY; CATALYZED ARYLATION; VERSATILE APPROACH; BETA-KETOESTERS; TRIFLUOROMETHYLATION; DIFLUOROMETHYLATION;
D O I
10.1021/acs.orglett.5b01997
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Disclosed herein is a dehydrosilylative difluoroamidation of alpha-Csp(3)-H of tetrahydroisoquinolines with alpha,alpha-difluoro-alpha-TMS-acetamides. The process, which occurs at ambient temperature in the absence of any transition metals, provides direct access to a broad range of alpha,alpha-difluoroacetamide-substituted tertiary amine derivatives in high yields. Moreover, the method was successfully applied in the Csp(3)-H-directed difluorophosphorylation and difluorocarboxylation under the same conditions.
引用
收藏
页码:4212 / 4215
页数:4
相关论文
共 50 条
  • [1] Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions
    Fier, Patrick S.
    Maloney, Kevin M.
    [J]. ORGANIC LETTERS, 2016, 18 (09) : 2244 - 2247
  • [2] Transition-Metal-Free Direct Trifluoromethylation and Perfluoroalkylation of Imidazopyridines under Mild Conditions
    Han, Shuaijun
    Gao, Xianying
    Wu, Qingsong
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (07) : 1559 - 1563
  • [3] Direct Transformation of Methyl Imines to -Iminonitriles under Mild and Transition-Metal-Free Conditions
    Chen, Feng
    Huang, Xiaoqiang
    Cui, Yuxin
    Jiao, Ning
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (34) : 11199 - 11202
  • [4] Odorless, Transition-Metal-Free N-Sulfenylation of Sulfoximines with Thiosulfonates under Mild Conditions
    Kang, Xiaokang
    Wang, Helin
    Zeng, Qingle
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (47)
  • [5] Transition-Metal-Free Highly Efficient Aerobic Oxidation of Sulfides to Sulfoxides under Mild Conditions
    Zhang, Hua
    Chen, Chunyu
    Liu, Renhua
    Xu, Qiang
    Zhao, Weiqie
    [J]. MOLECULES, 2010, 15 (01): : 83 - 92
  • [6] Base-Catalyzed Synthesis of Substituted Indazoles under Mild, Transition-Metal-Free Conditions
    Thome, Isabelle
    Besson, Claire
    Kleine, Tillmann
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) : 7509 - 7513
  • [7] Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions
    Wang, Peng-Fei
    Feng, Yi-Si
    Cheng, Zhi-Fei
    Wu, Qiu-Min
    Wang, Guang-Yu
    Liu, Liang-Liang
    Dai, Jian-Jun
    Xu, Jun
    Xu, Hua-Jian
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18): : 9314 - 9320
  • [8] C–F bond activation under transition-metal-free conditions
    HanJun Ai
    Xingxing Ma
    Qiuling Song
    XiaoFeng Wu
    [J]. Science China(Chemistry), 2021, (10) - 1659
  • [9] C–F bond activation under transition-metal-free conditions
    Han-Jun Ai
    Xingxing Ma
    Qiuling Song
    Xiao-Feng Wu
    [J]. Science China Chemistry, 2021, 64 (10) : 1630 - 1659
  • [10] Regioselective Synthesis of Phenoxathiin Derivatives under Transition-Metal-Free Conditions
    Hu, Fangdong
    Zhao, Xin
    Li, Yanqiu
    Feng, Lei
    Ma, Chen
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (07): : 966 - 970