Palladium-catalyzed desulfitative Sonogashira-Hagihara cross-couplings of arenesulfonyl chlorides and terminal alkynes

被引:67
|
作者
Dubbaka, SR [1 ]
Vogel, P [1 ]
机构
[1] Swiss Fed Inst Technol, EPFL, BCH, Lab Glycochem & Asymmetr Synth, CH-1015 Lausanne, Switzerland
关键词
alkynes; arenesulfonyl chlorides; C-C cross coupling; homogeneous catalysis; palladium; tri(t-butyl)phosphine ligand;
D O I
10.1002/adsc.200404146
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
For the first time, conditions have been found for the palladium-catalyzed desulfitative carbon-carbon cross-coupling of arenesulfonyl chlorides with aryl- and alkylacetylenes. Pd-2(dba)(3)/P(t-Bu)(3) and CuI provide the best catalyst for reactions in re-fluxing THF and in the presence of K2CO3.
引用
收藏
页码:1793 / 1797
页数:5
相关论文
共 50 条
  • [1] Recent progress in copper-free Sonogashira-Hagihara cross-couplings in water
    Struwe, Julia
    Ackermann, Lutz
    Gallou, Fabrice
    CHEM CATALYSIS, 2023, 3 (01):
  • [2] The palladium-catalyzed desulfitative cyanation of arenesulfonyl chlorides and sodium sulfinates
    Chen, Jianbin
    Sun, Yang
    Liu, Bin
    Liu, Dongfang
    Cheng, Jiang
    CHEMICAL COMMUNICATIONS, 2012, 48 (03) : 449 - 451
  • [3] Palladium-Catalyzed Sonogashira Cross-Couplings of (Hetero)Aryl Fluorosulfates
    Morrison, Kathleen M.
    Volpin, Giulio
    Kaldas, Sherif J.
    Holstein, Philipp M.
    Lubbesmeyer, Maximilian
    Ford, Mark James
    Guimond, Nicolas
    Stradiotto, Mark
    ORGANIC LETTERS, 2025, 27 (10) : 2456 - 2460
  • [4] Palladium-catalyzed stille cross-couplings of sulfonyl chlorides and organostannanes
    Dubbaka, SR
    Vogel, P
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) : 15292 - 15293
  • [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
    ORGANIC LETTERS, 2008, 10 (06) : 1147 - 1150
  • [7] Palladium-Catalyzed Desulfinative Cross-Couplings
    Gombert, Antoine de
    Willis, Michael C.
    TRENDS IN CHEMISTRY, 2020, 2 (09): : 865 - 866
  • [8] Palladium-catalyzed Suzuki cross-couplings of aryl chlorides in the presence of a triarylphosphine.
    Fu, GC
    Liu, SY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U399 - U399
  • [9] Neopentylphosphines as effective ligands in palladium-catalyzed cross-couplings of aryl bromides and chlorides
    Hill, Lensey L.
    Smith, Joanna A.
    Brown, William S.
    Moore, Lucas R.
    Guevera, Paul
    Pair, Emily S.
    Porter, Jake
    Chou, Joe
    Wolterman, Christopher J.
    Craciun, Raluca
    Dixon, David A.
    Shaughnessy, Kevin H.
    TETRAHEDRON, 2008, 64 (29) : 6920 - 6934
  • [10] Palladium-catalyzed cross-couplings of allylic phosphates
    Maslak, Veselin
    Tokic-Vujosevic, Zorana
    Saicic, Radomir N.
    TETRAHEDRON LETTERS, 2009, 50 (16) : 1858 - 1860