Transition-Metal-Free Sonogashira-Type Cross-Coupling of Alkynes with Fluoroarenes

被引:41
|
作者
Jin, Guanyi [1 ]
Zhang, Xuxue [1 ]
Cao, Song [1 ,2 ]
机构
[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
COPPER-FREE; GRIGNARD-REAGENTS; ARYL CHLORIDES; PALLADIUM; ALKYNYLATION; CATALYSTS; HYDRODEFLUORINATION; TRIFLUOROTOLUENES; POLYFLUOROARENES; ALKYLATION;
D O I
10.1021/ol401317m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, inexpensive, and efficient palladium-, copper-, ligand-, and amine-free Sonogashira-type cross-coupling reaction of terminal alkynes with unreactive aryl fluorides in the presence of sodium, sodium methoxide, and calcium hydroxide under the assistance of a Grignard reagent was developed. A plausible mechanism was also suggested.
引用
收藏
页码:3114 / 3117
页数:4
相关论文
共 50 条
  • [1] Transition-metal-free Sonogashira-type coupling reactions in water
    Appukkuttan, P
    Dehaen, W
    Van der Eycken, E
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) : 4713 - 4716
  • [2] Transition-Metal-Free Coupling Reactions: PPh3-Promoted Sonogashira-Type Cross-Couplings of Heteroaryl Halides with Terminal Alkynes
    Tian, Wan-Fa
    He, Ke-Han
    Li, Na
    Fen
    Liu
    Mai, Xi
    Feng, Li-Hua
    He, Yong-Qin
    [J]. CHEMISTRYSELECT, 2020, 5 (15): : 4496 - 4499
  • [3] Palladium-free Sonogashira-type cross-coupling reaction of bromoisoxazolines or N-alkoxyimidoyl bromides and alkynes
    Probst, N. P.
    Deprez, B.
    Willand, N.
    [J]. TETRAHEDRON LETTERS, 2016, 57 (10) : 1066 - 1070
  • [4] Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes
    Feng, Boya
    Yang, Yudong
    You, Jingsong
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (05) : 790 - 793
  • [5] Cu(I)-Catalyzed Macrocyclic Sonogashira-Type Cross-Coupling
    Santandrea, Jeffrey
    Bedard, Anne-Catherine
    Collins, Shawn K.
    [J]. ORGANIC LETTERS, 2014, 16 (15) : 3892 - 3895
  • [6] The first palladium-catalyzed desulfitative Sonogashira-type cross-coupling of (hetero)aryl thioethers with terminal alkynes
    Mehta, Vaibhav Pravinchandra
    Sharma, Anuj
    Van der Eycken, Erik
    [J]. ORGANIC LETTERS, 2008, 10 (06) : 1147 - 1150
  • [7] Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes
    He, Qing
    Wang, Liwen
    Liang, Yong
    Zhang, Zunting
    Wnuk, Stanislaw F.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9422 - 9427
  • [8] Gold and palladium combined for the Sonogashira-type cross-coupling of arenediazonium salts
    Panda, Biswajit
    Sarkar, Tarun K.
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (18) : 3131 - 3133
  • [9] Transition-metal-free regioselective cross-coupling of BODIPYs with thiols
    Lv, Fan
    Tang, Bing
    Hao, Erhong
    Liu, Qingyun
    Wang, Hua
    Jiao, Lijuan
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (11) : 1639 - 1642
  • [10] Copper- and base-free Sonogashira-type cross-coupling reaction of triarylantimony dicarboxylates with terminal alkynes under an aerobic condition
    Wang, Xuan
    Qin, Weiwei
    Kakusawa, Naoki
    Yasuike, Shuji
    Kurita, Jyoji
    [J]. TETRAHEDRON LETTERS, 2009, 50 (46) : 6293 - 6297