Synthesis of α-CF3 Amides via Palladium-Catalyzed Carbonylation of 2-Bromo-3,3,3-trifluoropropene

被引:6
作者
Wen, Xiao Rui [1 ]
Zhu, Wen Qing [1 ]
Zhang, Cai Lin [1 ]
Li, Hong [1 ]
Zhang, Jin [1 ]
Yang, Min Ge [1 ]
Kou, Yong Li [2 ]
Liu, Yu Xia [3 ]
Li, Yang [1 ]
机构
[1] Xian Polytech Univ, Sch Environm & Chem Engn, Xian 710048, Peoples R China
[2] Shaanxi Coal Chem Ind Technol Res Inst Co Ltd, Xian 710065, Peoples R China
[3] Northwest Univ, Coll Food Sci & Technol, Shaanxi Nat Carbohydrate Resource Engn Res Ctr, Xian 710127, Peoples R China
来源
ACS OMEGA | 2023年
基金
中国国家自然科学基金;
关键词
MANNICH-TYPE REACTION; BETA-LACTAMS; ASYMMETRIC FLUORINATION; AMINO-ACIDS; C(SP(3))-H; TRIFLUOROMETHYLATION; CYCLOADDITION; AMIDATION; ALKENES;
D O I
10.1021/acsomega.2c08206
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Amide compounds are important organic com-pounds, which play an important role in biomedical chemistry, materials science, life science, and other fields. The synthesis of alpha- CF3 amides, especially compounds containing 3-(trifluoromethyl)-1,3,4,5-tetrahydro-2H-benzo[b][1,4]diazepine-2-one, has long been a challenge due to the tensile properties and instability of the rings. Here, we report an example of palladium-catalyzed carbonylation of CF3-containing olefin to form alpha-CF3 acrylamide. By controlling the ligands, we can get different amide compounds as products. This method has good substrate adaptability and functional group tolerance.
引用
收藏
页码:7128 / 7134
页数:7
相关论文
共 50 条
  • [41] Synthesis of Cyclopenta[c]quinolines by Palladium-Catalyzed Cyclization of 3-Bromoindoles with Internal Alkynes via Spirocyclic Cyclopentadiene Intermediates
    Guo, Biao
    Lv, Jiaying
    Lu, Le
    Hua, Ruimao
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13) : 8984 - 8991
  • [42] Transformation of Anilines to 1-Azaspiro[4.5]decanes via Dearomatization and Palladium-Catalyzed aza-[3+2] Cycloaddition with Vinylcyclopropanes
    Xu, Tingxuan
    Hu, Jinhao
    He, Qiuqin
    Fan, Renhua
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [43] Palladium-catalyzed intramolecular [3C+2C] cycloaddition of alkylidenecyclopropanes to allenes
    Trillo, Beatriz
    Gulias, Moises
    Lopez, Fernando
    Castedo, Luis
    Mascarenas, Jose L.
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) : 2381 - 2384
  • [44] Synthesis of Fluoro- and Perfluoroalkyl Arenes via Palladium-Catalyzed [4+2] Benzannulation Reaction
    Zatolochnaya, Olga V.
    Gevorgyan, Vladimir
    ORGANIC LETTERS, 2013, 15 (10) : 2562 - 2565
  • [45] Palladium-Catalyzed Intramolecular C-H Difluoroalkylation: Synthesis of Substituted 3,3-Difluoro-2-oxindoles
    Shi, Shi-Liang
    Buchwald, Stephen L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) : 1646 - 1650
  • [46] Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Aziridines and α,β-Unsaturated Ketones
    Xu, Chao-Fan
    Zheng, Bao-Hui
    Suo, Jia-Jia
    Ding, Chang-Hua
    Hou, Xue-Long
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) : 1604 - 1607
  • [47] Highly efficient Cu(I)-catalyzed trifluoromethylation of aryl(heteroaryl) enol acetates with CF3 radicals derived from CF3SO2Na and TBHP at room temperature
    Lu, Yang
    Li, Yaming
    Zhang, Rong
    Jin, Kun
    Duan, Chunying
    JOURNAL OF FLUORINE CHEMISTRY, 2014, 161 : 128 - 133
  • [48] 3-Acylindoles via palladium-catalyzed regioselective arylation of electron-rich olefins with indoles
    Li, Yang
    Xue, Dong
    Lu, Wei
    Fan, Xiaogang
    Wang, Chao
    Xiao, Jianliang
    RSC ADVANCES, 2013, 3 (29) : 11463 - 11466
  • [49] Facile Synthesis of Quinoline-Substituted 3-Hydroxy-2-oxindoles and 3-Amino-2-oxindoles via a Palladium-Catalyzed Cascade Intramolecular Cyclization/Intermolecular Nucleophilic Addition Reaction
    Lin, Huawei
    Hu, Xinyan
    Han, Bing
    Yang, Xianru
    Deng, Yiwei
    Luo, Jiayi
    Ge, Yanqing
    Mao, Biming
    Wang, Chang
    Yuan, Chunhao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (05) : 3413 - 3418
  • [50] Palladium-Catalyzed [3+2+2] Cycloaddition Between Carbonyl-Tethered Alkylidenecyclopropanes and Isocyanates
    Rodino, Ricardo
    Mascarenas, Jose L.
    Lopez, Fernando
    HELVETICA CHIMICA ACTA, 2025,