Visible Light Catalyzed Reductive Cross-Coupling of α-CF3-alkyl Bromide and Alkynyl Bromide

被引:4
作者
Tian, Yiqiang [1 ]
Li, Yi [1 ]
Zhang, Chun [1 ]
机构
[1] Tianjin Univ, Inst Mol Plus, Fac Med, Sch Pharmaceut Sci & Technol,Dept Chem, 92 Weijin Rd, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金;
关键词
Visiable light catalysis; C-C bond formation; Reductive cross-coupling; Trifluoromethyl group; Alkynyl group; Radicals; Organohalides; Photochemistry; AMINOALKYL RADICALS; TRIFLUOROMETHYLATION; ELECTROPHILES; DERIVATIVES; ACTIVATION; ACIDS;
D O I
10.1002/cjoc.202400402
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Traditional reduction coupling reactions of two bromides typically rely on transition metal catalysis. Here, we introduce the development of a visible-light catalytic direct reduction coupling reaction between alpha-CF3-alkyl bromides and alkynyl bromides to access valuable organic frameworks. Our research confirms the excellent compatibility of this reaction with various functional groups, which could be used to modify the substrate with biologically active molecular fragments. Mechanistic investigations, including control experiments, fluorescence quenching studies, and light-switching experiments, have provided insights into the reaction mechanism. This study paves the way for the application of visible-light catalysis in diverse synthetic transformations, offering a sustainable and efficient approach to organic synthesis.
引用
收藏
页码:2479 / 2484
页数:6
相关论文
共 66 条
[21]   Asymmetric construction of allylicstereogenic carbon center featuring atrifluoromethyl group via enantioselective reductive fluoroalkylation [J].
Jin, Ruo-Xing ;
Wu, Bing-Bing ;
Bian, Kang-Jie ;
Yu, Jian-Liang ;
Dai, Jing-Cheng ;
Zuo, Ya-Wen ;
Zhang, Yi-Fan ;
Wang, Xi-Sheng .
NATURE COMMUNICATIONS, 2022, 13 (01)
[22]   Elemental-Sulfur-Enabled Divergent Synthesis of Disulfides, Diselenides, and Polythiophenes from β-CF3-1,3-Enynes [J].
Jin, Shengnan ;
Li, Shi-Jun ;
Ma, Xingxing ;
Su, Jianke ;
Chen, Haohua ;
Lan, Yu ;
Song, Qiuling .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (02) :881-888
[23]   Trifluorodiazoethane: A versatile building block to access trifluoromethylated heterocycles [J].
Kumar, Anuj ;
Khan, Waqas Ahmad ;
Ahamad, Shakir ;
Mohanan, Kishor .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (04) :607-632
[24]   Nickel-Catalyzed Direct Trifluoroethylation of Aryl Iodides with 1,1,1-Trifluoro-2-Iodoethane via Reductive Coupling [J].
Li, Han ;
Sheng, Jie ;
Liao, Guang-Xu ;
Wu, Bing-Bing ;
Ni, Hui-Qi ;
Li, Yan ;
Wang, Xi-Sheng .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (23) :5363-5367
[25]   Catalytic Asymmetric Homologation of 4-Substituted Cyclohexanones with CF3CHN2: Enantioselective Synthesis of α-Trifluoromethyl Cycloheptanones [J].
Li, Shu-Sen ;
Sun, Shuo ;
Wang, Jianbo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (06)
[26]   Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF3 and an Alkyl Group [J].
Liang, Yufan ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (30) :9523-9526
[27]   Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent [J].
Liang, Yufan ;
Fu, Gregory C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (31) :9047-9051
[28]   General and Modular Access to Enantioenriched α-Trifluoromethyl Ketones via Nickel-Catalyzed Reductive Trifluoroalkylation [J].
Lin, Dengkai ;
Chen, Yongzhi ;
Dong, Zhan ;
Pei, Pan ;
Ji, Haiting ;
Tai, Lanzhu ;
Chen, Liang-An .
CCS CHEMISTRY, 2023, 5 (06) :1386-1397
[29]   Empowering a transition-metal-free coupling between alkyne and alkyl iodide with light in water [J].
Liu, Wenbo ;
Li, Lu ;
Li, Chao-Jun .
NATURE COMMUNICATIONS, 2015, 6
[30]   Halogen-Atom Transfer Enabled Catalytic Enantioselective Coupling to Chiral Trifluoromethylated Alkynes via Dual Nickel and Photocatalysis [J].
Lu, Shanya ;
Hu, Zihao ;
Wang, Dong ;
Xu, Tao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (28)