Recycled Pd/C-Catalyzed Heck Reaction of 2-Iodoanilines under Ligand-Free Conditions

被引：7
作者：
Zhou, Xiao-Yu [1 ]
Chen, Xia [1 ]
Wang, Liang-Guang [2 ]
机构：
[1] Liupanshui Normal Univ, Coll Chem & Mat Engn, Liupanshui 553004, Peoples R China
[2] Anshun Univ, Coll Chem & Chem Engn, Anshun 561000, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 24期
关键词：
palladium; heterogeneous catalysis; Heck reaction; ligand-free; 2-iodoaniline; CROSS-COUPLING REACTIONS; ARYL CHLORIDES; IONIC LIQUIDS; C-C; ORGANIC-SYNTHESIS; MILD CONDITIONS; PALLADIUM; BROMIDES; TEMPERATURE; CYCLIZATION;
D O I：
10.1055/s-0036-1590895
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Recyclable Pd/C-catalyzed Heck reaction of 2-iodoanilines with acrylate has been developed. The reaction occurred readily in 1,4-dioxane using Pd/C (10 wt%) as catalyst under ligand-free conditions, and the cross-coupling products were obtained with medium to high yield. Gram-scale reactions and recycling of the catalyst were also demonstrated.
引用
收藏
页码：5364 / 5370
页数：7
相关论文
共 52 条
  • [1] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [2] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [3] Recyclable Hybrid Silica-Based Catalysts Derived from Pd-NHC Complexes for Suzuki, Heck and Sonogashira Reactions
    Borja, Guadalupe
    Monge-Marcet, Amalia
    Pleixats, Roser
    Parella, Teodor
    Cattoen, Xavier
    Man, Michel Wong Chi
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (19) : 3625 - 3635
  • [4] C-C Bond-Forming Lyases in Organic Synthesis
    Brovetto, Margarita
    Gamenara, Daniela
    Saenz Mendez, Patricia
    Seoane, Gustavo A.
    [J]. CHEMICAL REVIEWS, 2011, 111 (07) : 4346 - 4403
  • [5] Copper bronze catalyzed Heck reaction in ionic liquids
    Calò, V
    Nacci, A
    Monopoli, A
    Ieva, E
    Cioffi, N
    [J]. ORGANIC LETTERS, 2005, 7 (04) : 617 - 620
  • [6] The Heck reaction in ionic liquids: A multiphasic catalyst system
    Carmichael, AJ
    Earle, MJ
    Holbrey, JD
    McCormac, PB
    Seddon, KR
    [J]. ORGANIC LETTERS, 1999, 1 (07) : 997 - 1000
  • [7] Poly(ethylene glycol) (PEG) as a reusable solvent medium for organic synthesis. Application in the Heck reaction
    Chandrasekhar, S
    Narsihmulu, C
    Sultana, SS
    Reddy, NR
    [J]. ORGANIC LETTERS, 2002, 4 (25) : 4399 - 4401
  • [8] Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds
    Cherney, Alan H.
    Kadunce, Nathaniel T.
    Reisman, Sarah E.
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9587 - 9652
  • [9] Unique tandem Heck-lactamization naphthyridinone ring formation between acrylanilides and halogenated pyridines
    Cvetovich, Raymond J.
    Reamer, Robert A.
    DiMichele, Lisa
    Chung, John Y. L.
    Chilenski, Jennifer R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) : 8610 - 8613
  • [10] Remarkable dendritic effect in the polymer-supported catalysis of the Heck arylation of olefins
    Dahan, A
    Portnoy, M
    [J]. ORGANIC LETTERS, 2003, 5 (08) : 1197 - 1200
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