Cu/Picolinamides-Catalyzed Coupling of (Hetero)aryl Halides with Secondary Phosphine Oxides and Phosphite†

被引:8
作者
Fang, Chao [1 ]
Wei, Bangguo [1 ]
Ma, Dawei [2 ]
机构
[1] Fudan Univ, Sch Pharm, Dept Nat Med, 826 Zhangheng Rd, Shanghai 201203, Peoples R China
[2] Univ Chinese Acad Sci, Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,State Key Lab Bioorgan, 345 Lingling Lu, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Synthetic methods; Cross-Coupling; Aryl halides; Copper; Aryl phosphine oxides; P BOND FORMATION; ARYLBORONIC ACIDS; ROOM-TEMPERATURE; ARYL HALIDES; CHLORIDES; ARYLATION; DIPHENYLPHOSPHINE; PHOSPHORYLATION; BROMIDES;
D O I
10.1002/cjoc.202100354
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Main observation and conclusion Some 4-hydroxy-picolinic acid derived amides were revealed as more efficient ligands for Cu-catalyzed coupling of (hetero)aryl halides with secondary phosphine oxides and phosphites. Only 3-5 mol% CuI and ligands were required to ensure coupling with a number of (hetero)aryl bromides and iodides to complete at 120 C-o in 10-20 h.
引用
收藏
页码:2957 / 2961
页数:5
相关论文
共 50 条
  • [31] Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides
    Zhang, Qingchen
    Wang, Xuan
    Qian, Qun
    Gong, Hegui
    SYNTHESIS-STUTTGART, 2016, 48 (17): : 2829 - 2836
  • [32] Mild Cobalt-Catalyzed Negishi Cross-Couplings of (Hetero)arylzinc Reagents with (Hetero)aryl Halides
    Haas, Diana
    Hammann, Jeffrey M.
    Lutter, Ferdinand H.
    Knochel, Paul
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (11) : 3809 - 3812
  • [33] Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media
    Cohen, Daniel T.
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2015, 17 (02) : 202 - 205
  • [34] Copper-Catalyzed Dynamic Kinetic Asymmetric P-C Coupling of Secondary Phosphine Oxides and Aryl Iodides
    Kang, Jie
    Ding, Kang
    Ren, Si-Mu
    Su, Bo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (25)
  • [35] Paired Electrolysis Enables Reductive Heck Coupling of Unactivated (Hetero)Aryl Halides and Alkenes
    Lai, Yihuan
    Milner, Phillip J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (38)
  • [36] Light-promoted, nickel-catalyzed C-N coupling of (hetero)aryl halides with benzophenone hydrazone for the synthesis of nitrogen-containing heterocycles
    Li, Fei
    Lu, Huan-huan
    Liao, Huijuan
    Xiong, Weikang
    Dong, Jianyang
    Li, Gang
    Xue, Dong
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (21): : 6089 - 6095
  • [37] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides
    Qian, Qun
    Zang, Zhenhua
    Wang, Shulin
    Chen, Yang
    Lin, Kunhua
    Gong, Hegui
    SYNLETT, 2013, 24 (05) : 619 - 624
  • [38] Cobalt-Catalyzed Cross-Coupling Reactions Aryl Halides
    Gosmini, Corinne
    Moncomble, Aurelien
    ISRAEL JOURNAL OF CHEMISTRY, 2010, 50 (5-6) : 568 - 576
  • [39] Palladium-Catalyzed Decarboxylative Coupling of Quinolinone-3-Carboxylic Acids and Related Heterocyclic Carboxylic Acids with (Hetero)aryl Halides
    Messaoudi, Samir
    Brion, Jean-Daniel
    Alami, Mouad
    ORGANIC LETTERS, 2012, 14 (06) : 1496 - 1499
  • [40] Solvent-free palladium-catalyzed C-O cross-coupling of (hetero)aryl halides with primary alcohols
    Rzhevskiy, Sergey A.
    Topchiy, Maxim A.
    Bogachev, Vasilii N.
    Minaeva, Lidiya I.
    Cherkashchenko, Ilia R.
    V. Lavrov, Konstantin
    Sterligov, Grigorii K.
    Nechaev, Mikhail S.
    Asachenko, Andrey F.
    MENDELEEV COMMUNICATIONS, 2022, 32 (02) : 258 - 259