Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

被引：12
|
作者：
Ibrahim, Mansur B. [1 ]
El Ali, Bassam [1 ]
Malik, Imran [1 ]
Fettouhi, Mohammed [1 ]
机构：
[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 05期
关键词：
Palladium-bis(oxazoline); Sonogashira coupling; Diiodobenzene; Alkyl alkynes; Dialkynes; CROSS-COUPLING REACTIONS; COPPER-FREE; ARYL BROMIDES; SUZUKI-MIYAURA; TERMINAL ALKYNES; EFFICIENT; HECK; CHLORIDES; COMPLEX; LIGAND;
D O I：
10.1016/j.tetlet.2015.12.086
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH3CN-H2O solvent system allowed for the cross -coupling reactions to proceed at room temperature or 60 degrees C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross -coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：554 / 558
页数：5
相关论文
共 50 条
  • [31] Palladium-catalyzed cyclotrimerization of alkynes
    Zhou, L
    Jiang, HF
    Huang, JM
    Tang, JY
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (01) : 1 - 8
  • [32] PALLADIUM-CATALYZED HYDROCARBOXYLATION OF ALKYNES
    ZARGARIAN, D
    ALPER, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 319 - INOR
  • [33] Dual role of nucleophiles in palladium-catalyzed Heck, Stille, and Sonogashira reactions
    Jutand, A
    PURE AND APPLIED CHEMISTRY, 2004, 76 (03) : 565 - 576
  • [34] Synthesis of β- and γ-carbolines by the palladium-catalyzed iminoannulation of internal alkynes
    Zhang, HM
    Larock, RC
    ORGANIC LETTERS, 2001, 3 (20) : 3083 - 3086
  • [35] Palladium-Catalyzed Carbothiolation of Alkenes and Alkynes for the Synthesis of Heterocycles
    Delcaillau, Tristan
    Schmitt, Hendrik L.
    Boehm, Philip
    Falk, Eric
    Morandi, Bill
    ACS CATALYSIS, 2022, 12 (10) : 6081 - 6091
  • [36] Synthesis of indenes by the palladium-catalyzed carboannulation of internal alkynes
    Zhang, DH
    Yum, EK
    Liu, ZJ
    Larock, RC
    ORGANIC LETTERS, 2005, 7 (22) : 4963 - 4966
  • [37] Allyl stannanes as electrophiles or nucleophiles in the palladium-catalyzed reactions with alkynes
    Martín-Matute, B
    Buñuel, E
    Méndez, M
    Nieto-Oberhuber, C
    Cárdenas, DJ
    Echavarren, AM
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) : 410 - 419
  • [38] New palladium-catalyzed reactions of unsaturated triflates with alkenes and alkynes
    Cacchi, S
    PURE AND APPLIED CHEMISTRY, 1996, 68 (01) : 45 - 52
  • [39] Palladium-Catalyzed Carbonylative Synthesis of Functionalized Benzimidazopyrimidinones
    Mancuso, Raffaella
    Veltri, Lucia
    Russo, Patrizio
    Grasso, Giuseppe
    Cuocci, Corrado
    Romeo, Roberto
    Gabriele, Bartolo
    SYNTHESIS-STUTTGART, 2018, 50 (02): : 267 - 277
  • [40] Palladium-catalyzed reactions of siliranes with alkynes to produce silirenes.
    Palmer, WS
    Woerpel, KA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 28 - INOR
12345