Visible-Light-Induced Trifluoromethylation/Cyclization of 1,7-Enynes in Continuous Flow

被引:19
|
作者
Zhuang, Kaiqiang [1 ]
Cui, Yusheng [1 ]
Yuan, Xin [1 ]
Qin, Longzhou [1 ]
Sun, Qi [1 ]
Duan, Xiu [1 ]
Chen, Lin [1 ]
Zhang, Xinpeng [1 ]
Qiu, Jiangkai [1 ]
Guo, Kai [1 ]
机构
[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Peoples R China
来源
基金
中国国家自然科学基金;
关键词
photoredox-catalyzed; trifluoromethylation; cyclization; 1,7-enynes; continuous-flow; CATALYZED CASCADE CYCLIZATION; OXIDATIVE TRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; FACILE SYNTHESIS; FLUORINE; PERFLUOROALKYLATION; FUNCTIONALIZATION; HETEROARENES; N-ENYNES; ACCESS;
D O I
10.1021/acssuschemeng.0c03745
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the present study, we describe the successful development of a photoredox-catalyzed trifluoromethylation/cyclization of 1,7-enynes in a continuous-flow regime for the generation of several CF 3 -containing heterocyclic scaffolds. When using this protocol, a readily prepared Ph2SCF3OTf reagent was employed as the trifluoromethylation reagent, and various benzo[j]phenanthridines and indeno[1,2-c]quinolines were obtained in good to moderate yields. This transformation featured mild reaction conditions, a broad substrate scope, and ease of scale-up. Moreover, the continuous-flow processing in a photomicroreactor accelerated the reaction (5 min reaction time) and increased the product yields (up to 89%).
引用
收藏
页码:11729 / 11736
页数:8
相关论文
共 50 条
  • [21] Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water
    Jana, Sadhan
    Verma, Ajay
    Kadu, Rahul
    Kumar, Sangit
    CHEMICAL SCIENCE, 2017, 8 (09) : 6633 - 6644
  • [22] Gold-catalyzed cyclizations of 1,7-enynes
    Cabello, Noemi
    Rodriguez, Cristina
    Echavarren, Antonio M.
    SYNLETT, 2007, (14) : 2308 - 2308
  • [23] Transition-Metal Controlled Diastereodivergent Radical Cyclization/Azidation Cascade of 1,7-Enynes
    Zhao, Yingying
    Hu, Yancheng
    Wang, Haolong
    Li, Xincheng
    Wan, Boshun
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (10): : 4412 - 4420
  • [24] Gold-catalyzed cyclizations of 1,7-enynes
    Cabello, Noemi
    Rodriguez, Cristina
    Echavarren, Antonio M.
    SYNLETT, 2007, (11) : 1753 - 1758
  • [25] A Facile Synthesis of Functionalized Benzofurans via Visible-Light-Induced Tandem Cyclization of 1,6-Enynes with Disulfides
    Li, Xuezhi
    Xu, Zhaoliang
    Wang, Lei
    Wang, Fang
    Yang, Jianguo
    Li, Pinhua
    CHEMPHOTOCHEM, 2021, 5 (02): : 142 - 148
  • [26] Visible-Light-Induced Photocatalyst-Free Radical Trifluoromethylation
    Li, Yufei
    Liang, Xin
    Niu, Kaikai
    Gu, Jun
    Liu, Fang
    Xia, Qing
    Wang, Qingmin
    Zhang, Weihua
    ORGANIC LETTERS, 2022, 24 (32) : 5918 - 5923
  • [27] Metal-Free Visible-Light-Induced Trifluoromethylation Reactions
    Park, Gwi-Rim
    Choi, Yeojin
    Choi, Myung Gil
    Chang, Suk-Kyu
    Cho, Eun Jin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) : 436 - 440
  • [28] CYCLIZATION REACTIONS OF MOLYBDENUM AND CHROMIUM CARBENE COMPLEXES WITH 1,6-ENYNES AND 1,7-ENYNES - EFFECT OF TETHER LENGTH AND COMPOSITION
    HARVEY, DF
    LUND, KP
    NEIL, DA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) : 8424 - 8434
  • [29] A NOVEL CYCLOALKYLATION OF 1,6-ENYNES AND 1,7-ENYNES WITH STABILIZED PRONUCLEOPHILES
    TROST, BM
    ZHI, L
    IMI, K
    TETRAHEDRON LETTERS, 1994, 35 (09) : 1361 - 1364
  • [30] Metal-free oxidative hydrophosphinylation of 1,7-enynes
    Zhu, Yi-Long
    Wang, De-Cai
    Jiang, Bo
    Hao, Wen-Juan
    Wei, Ping
    Wang, Ai-Fang
    Qiu, Jiang-Kai
    Tu, Shu-Jiang
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (03): : 385 - 393