A Robust and Broadly Applicable Cobalt-Catalyzed Cross-Coupling of Functionalized Bench-Stable Organozinc Pivalates with Unsaturated Halides

被引:32
|
作者
Hammann, Jeffrey M. [1 ]
Lutter, Ferdinand H. [1 ]
Haas, Diana [1 ]
Knochel, Paul [1 ]
机构
[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany
关键词
cobalt; cross-coupling; N-heterocycles; zinc; zinc pivalate; LATE-STAGE FUNCTIONALIZATION; C-H FUNCTIONALIZATION; (HETERO)ARYLZINC REAGENTS; ACTIVE CATALYST; ZINC REAGENTS; ARYL; DIVERSIFICATION; ARYLMAGNESIUM; MILD; BORYLATION;
D O I
10.1002/anie.201610324
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report a robust and broadly applicable CoCl2-catalyzed cross-coupling between functionalized aryl and heteroaryl zinc pivalates and various electron-poor aryl and heteroaryl halides (X = Cl, Br, I). Couplings with (E)- or (Z)-bromo- or iodo-alkenes proceed with retention of configuration. Also, alkynyl bromides react with arylzinc pivalates providing arylated alkynes.
引用
收藏
页码:1082 / 1086
页数:5
相关论文
共 50 条
  • [1] Cobalt-Catalyzed Cross-Coupling of Organozinc Halides with Bromoalkynes
    Corpet, Martin
    Bai, Xian-Zhou
    Gosmini, Corinne
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 2937 - 2942
  • [2] Cobalt-Catalyzed Cross-Couplings of Bench-Stable Alkynylzinc Pivalates with (Hetero)Aryl and Alkenyl Halides
    Hammann, Jeffrey M.
    Thomas, Lucie
    Chen, Yi-Hung
    Haas, Diana
    Knochel, Paul
    [J]. ORGANIC LETTERS, 2017, 19 (14) : 3847 - 3850
  • [3] Large-Scale Cobalt-Catalyzed Cross-Couplings of Functionalized Bench-Stable Arylzinc Pivalates with (Hetero)Aryl and Alkenyl Halides
    Hofmayer, Maximilian S.
    Hammann, Jeffrey M.
    Lutter, Ferdinand H.
    Knochel, Paul
    [J]. SYNTHESIS-STUTTGART, 2017, 49 (17): : 3925 - 3930
  • [4] Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides
    Lutter, Ferdinand H.
    Grokenberger, Lucie
    Spiess, Philipp
    Hammann, Jeffrey M.
    Karaghiosoff, Konstantin
    Knochel, Paul
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5546 - 5550
  • [5] Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides
    Lutter, Ferdinand H.
    Grokenberger, Lucie
    Spieβ, Philipp
    Hammann, Jeffrey M.
    Karaghiosoff, Konstantin
    Knochel, Paul
    [J]. Advanced Materials, 2020, 132 (14) : 5591 - 5595
  • [6] Cobalt-Catalyzed Cross-Coupling Reactions Aryl Halides
    Gosmini, Corinne
    Moncomble, Aurelien
    [J]. ISRAEL JOURNAL OF CHEMISTRY, 2010, 50 (5-6) : 568 - 576
  • [7] Cobalt-Catalyzed Cross-Couplings and Electrophilic Aminations using Organozinc Pivalates
    Lutter, Ferdinand H.
    Grassl, Simon
    Grokenberger, Lucie
    Hofmayer, Maximilian S.
    Chen, Yi-Hung
    Knochel, Paul
    [J]. CHEMCATCHEM, 2019, 11 (21) : 5188 - 5197
  • [8] Cobalt-catalyzed electrochemical cross-coupling of functionalized phenyl halides with 4-chloroquinoline derivatives
    Le Gall, E
    Gosmini, C
    Nédélec, JY
    Périchon, J
    [J]. TETRAHEDRON LETTERS, 2001, 42 (02) : 267 - 269
  • [9] Mechanochemical Pd-Catalyzed Cross-Coupling of Arylhalides and Organozinc Pivalates
    Carny, Tomas
    Penaska, Tibor
    Andrejcak, Samuel
    Sebesta, Radovan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (58)
  • [10] Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides
    Duong, Hung A.
    Wu, Wenqin
    Teo, Yu-Yuan
    [J]. ORGANOMETALLICS, 2017, 36 (22) : 4363 - 4366