Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions

被引：49
|
作者：
Stein, A. L. [1 ]
Bilheri, F. N. [1 ]
Zeni, G. [1 ]
机构：
[1] CCNE, UFSM, Lab Sintese Reatividade Avaliacao Farmacol & Texi, BR-97105900 Santa Maria, RS, Brazil
来源：
CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 85期
关键词：
COPPER-CATALYZED SYNTHESIS; DIPHENYL DISELENIDE; ARYLBORONIC ACIDS; SE-SE; DIARYL DISULFIDES; ARYL IODIDE; BOND; CLEAVAGE; DICHALCOGENIDES; CHALCOGENATION;
D O I：
10.1039/c5cc06347g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We reported herein the regio- and stereoselective palladium-catalyzed cross-coupling reactions of unsaturated organoselenides with Sonogashira, Suzuki, Negishi and Kumada partners. The reactions were in general carried out with Pd(PPh3)(4) (10 mol%), in DMF at 80 degrees C to afford the cross-coupling products in good yields. This strategy tolerated a wide range of substrates, such as alkynyl, vinyl, aryl and heteroaryl selenides with a variety of sensitive functional groups and gave the cross-coupling products in good yields.
引用
收藏
页码：15522 / 15525
页数：4
相关论文
共 50 条
  • [1] Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides
    Walla, P
    Kappe, CO
    [J]. CHEMICAL COMMUNICATIONS, 2004, (05) : 564 - 565
  • [2] Total Synthesis of Isodesmosine by Stepwise, Regioselective Negishi and Sonogashira Cross-Coupling Reactions
    Koseki, Yohei
    Sugimura, Takanori
    Ogawa, Keita
    Suzuki, Rina
    Yamada, Haruka
    Suzuki, Noriyuki
    Masuyama, Yoshiro
    Lin, Yong Y.
    Usuki, Toyonobu
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (18) : 4024 - 4032
  • [3] Sequential Sonogashira and Suzuki cross-coupling reactions in the indole and indazole series
    Witulski, B
    Azcon, JR
    Alayrac, C
    Arnautu, A
    Collot, V
    Rault, S
    [J]. SYNTHESIS-STUTTGART, 2005, (05): : 771 - 780
  • [4] Phosphaalkenes palladium(II) complexes in the Suzuki and Sonogashira cross-coupling reactions
    Deschamps, Bernard
    Le Goff, Xavier
    Ricard, Louis
    Le Floch, Pascal
    [J]. HETEROATOM CHEMISTRY, 2007, 18 (04) : 363 - 371
  • [5] Total synthesis of the COPD biomarker desmosine via Sonogashira and Negishi cross-coupling reactions
    Yanuma, Hiroto
    Usuki, Toyonobu
    [J]. TETRAHEDRON LETTERS, 2012, 53 (44) : 5920 - 5922
  • [6] Synthesis of differentially substituted hexaethynylbenzenes based on tandem Sonogashira and Negishi cross-coupling reactions
    Sonoda, M
    Inaba, A
    Itahashi, K
    Tobe, Y
    [J]. ORGANIC LETTERS, 2001, 3 (15) : 2419 - 2421
  • [7] Application of hindered ether solvents for palladium catalyzed Suzuki-Miyaura, Sonogashira and cascade Sonogashira cross-coupling reactions
    Sangon, Suwiwat
    Supanchaiyamat, Nontipa
    Sherwood, James
    Macquarrie, Duncan J.
    Noppawan, Pakin
    Hunt, Andrew J.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (12) : 2603 - 2609
  • [8] Transition metal nanoparticles as nanocatalysts for Suzuki, Heck and Sonogashira cross-coupling reactions
    Ashraf, Muhammad
    Ahmad, Muhammad Sohail
    Inomata, Yusuke
    Ullah, Nisar
    Tahir, Muhammad Nawaz
    Kida, Tetsuya
    [J]. COORDINATION CHEMISTRY REVIEWS, 2023, 476
  • [9] Synthesis of desmosine-BSA/KLH conjugates via Sonogashira/Negishi cross-coupling reactions
    Miyagi, Seiya
    Yokoo, Reiko
    Tanigawa, Takahiro
    Pitna, Dinda B.
    Hirose, Mika
    Usuki, Toyonobu
    [J]. TETRAHEDRON LETTERS, 2022, 90
  • [10] Recent Developments in Negishi Cross-Coupling Reactions
    Haas, Diana
    Hammann, Jeffrey M.
    Greiner, Robert
    Knochel, Paul
    [J]. ACS CATALYSIS, 2016, 6 (03): : 1540 - 1552
12345