Ligand-Free Nickel-Catalyzed Reductive Allylic Defluorinative Cross-Coupling of α-Trifluoromethyl Alkenes with Epoxides

被引：3
|
作者：
Lin, Zhiyang [1 ,2 ]
Lan, Yun [1 ,2 ]
Wang, Chuan [1 ,2 ,3 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China
来源：
SYNLETT | 2021年 / 32卷 / 15期
基金：
中国国家自然科学基金;
关键词：
nickel catalysis; epoxides; difluoroalkenes; defluorination; ring opening; F BOND ACTIVATION; NUCLEOPHILIC 5-ENDO-TRIG CYCLIZATION; FUNCTIONALIZED GEM-DIFLUOROALKENES; DIFLUOROMETHYL 2-PYRIDYL SULFONE; C-F; DIAZO-COMPOUNDS; ORGANOLITHIUM REAGENTS; BIOLOGICAL-ACTIVITY; CONCISE SYNTHESIS; DIFLUOROOLEFINATION;
D O I：
10.1055/s-0040-1707170
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report a reductive allylic defluorinative reaction of.-trifluoromethyl alkenes with terminal epoxides, which consists of an iodide-mediated regioselective ring opening and a nickel-catalyzed radical-type cross-coupling, providing diverse tertiary gemdifluorobishomoallylic alcohols in moderate to high yields. Notably, this reaction is conducted under mild conditions and requires no external ligand or proton donor.
引用
收藏
页码：1547 / 1550
页数：4
相关论文
共 50 条
  • [31] Nickel-Catalyzed Hydrotrifluoroalkylation of Alkynes to Construct Allylic Trifluoromethyl Terminal Alkenes
    Zhang, Ting
    Zuo, Ya-Wen
    Jin, Ruo-Xing
    Zhang, Yi-Fan
    Wang, Xi-Sheng
    Wu, Bing-Bing
    ORGANIC LETTERS, 2023, 25 (19) : 3578 - 3584
  • [32] Ligand-Controlled Nickel-Catalyzed Reductive Relay Cross-Coupling of Alkyl Bromides and Aryl Bromides
    Peng, Long
    Li, Yuqiang
    Li, Yangyang
    Wang, Wang
    Pang, Hailiang
    Yin, Guoyin
    ACS CATALYSIS, 2018, 8 (01): : 310 - 313
  • [33] Reductive Allylic Defluorinative Cross-Coupling Enabled by Ni/Ti Cooperative Catalysis
    Lin, Zhiyang
    Lan, Yun
    Wang, Chuan
    ORGANIC LETTERS, 2019, 21 (20) : 8316 - 8322
  • [34] Nickel-Catalyzed Allylic Defluorinative Cross-Electrophile Coupling with Cycloalkyl Silyl Peroxides as the Alkyl Source
    Dong, Haiyan
    Lin, Zhiyang
    Wang, Chuan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (01): : 892 - 903
  • [35] Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles
    Kadunce, Nathaniel T.
    Reisman, Sarah E.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (33) : 10480 - 10483
  • [36] Nickel-Catalyzed Desulfonylative Reductive Cross-Coupling of Aryl Sulfones with Aryl Bromides
    Huang, Xinmiao
    Tang, Ling
    Song, Zhiyong
    Jiang, Shuangshuang
    Liu, Xianmao
    Ma, Ming
    Chen, Bo
    Ma, Yuanhong
    ORGANIC LETTERS, 2023, : 1198 - 1203
  • [37] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides
    Sumida, Yuto
    Sumida, Tomoe
    Hosoya, Takamitsu
    SYNTHESIS-STUTTGART, 2017, 49 (16): : 3590 - 3601
  • [38] Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides
    Wang, Wei
    Yao, Ken
    Wu, Fan
    SYNLETT, 2022, 33 (04) : 361 - 366
  • [39] Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides
    Gu, Jun
    Qiu, Canbin
    Lu, Wenbin
    Qian, Qun
    Lin, Kunhua
    Gong, Hegui
    SYNTHESIS-STUTTGART, 2017, 49 (08): : 1867 - 1873
  • [40] Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides
    DeLano, Travis J.
    Dibrell, Sara E.
    Lacker, Caitlin R.
    Pancoast, Adam R.
    Poremba, Kelsey E.
    Cleary, Leah
    Sigman, Matthew S.
    Reisman, Sarah E.
    CHEMICAL SCIENCE, 2021, 12 (22) : 7758 - 7762
12345