Pd/C: An efficient and reusable catalyst for the synthesis of flavones via carbonylation of aryl halides

被引:5
作者
Lei, Yizhu [1 ]
Li, Zhi [1 ]
Wan, Yali [1 ]
Zhou, Xiao-Yu [1 ]
Li, Guangxing [2 ]
Shi, Kaiyi [1 ]
机构
[1] Liupanshui Normal Univ, Sch Chem & Mat Engn, Liupanshui 553004, Guizhou, Peoples R China
[2] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Luoyu Rd 1037, Wuhan 430074, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
aryl halide; carbonylation; flavone; heterogeneous catalysis; palladium on charcoal; POROUS ORGANIC POLYMER; ONE-POT SYNTHESIS; HETEROGENEOUS CATALYST; 4-COMPONENT SYNTHESIS; COUPLING REACTIONS; TERTIARY AMIDES; PALLADIUM; AMINOCARBONYLATION; CHLORIDES; IODIDES;
D O I
10.1002/aoc.4163
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This work describes an efficient and mild approach for the synthesis of flavones via catalytic carbonylation of aryl halides with 2-hydroxyacetophenone using the commercial Pd/C as an efficient, heterogeneous and recyclable catalyst. Under balloon pressure of CO, 0.6mol% Pd/C is sufficient for moderate yields of flavones for the carbonylation of aryl iodides under phosphine-free conditions and aryl bromides in the presence of phosphine ligand. The catalyst is easily separable and shows significant recyclability. Moreover, the reaction mechanism was discussed, and a possible mechanism that contains two different cyclisation pathways was proposed.
引用
收藏
页数:7
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共 43 条
  • [1] Access to Flavones via a Microwave-Assisted, One-Pot Sonogashira-Carbonylation-Annulation Reaction
    Awuah, Emelia
    Capretta, Alfredo
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3210 - 3213
  • [2] An efficient one-pot synthesis of flavones
    Chee, Chin Fei
    Buckle, Michael J. C.
    Abd Rahman, Noorsaadah
    [J]. TETRAHEDRON LETTERS, 2011, 52 (24) : 3120 - 3123
  • [3] Pd/C-catalyzed carbonylative C-H activation with DMF as the CO source
    Chen, Jianbin
    Natte, Kishore
    Wu, Xiao-Feng
    [J]. TETRAHEDRON LETTERS, 2015, 56 (46) : 6413 - 6416
  • [4] Metal-organic frameworks: versatile heterogeneous catalysts for efficient catalytic organic transformations
    Chughtai, Adeel H.
    Ahmad, Nazir
    Younus, Hussein A.
    Laypkov, A.
    Verpoort, Francis
    [J]. CHEMICAL SOCIETY REVIEWS, 2015, 44 (19) : 6804 - 6849
  • [5] Colquhoun H. M., 1991, CARBONYLATION DIRECT, P236
  • [6] Heterogeneous Catalysis: A Central Science for a Sustainable Future
    Friend, Cynthia M.
    Xu, Bingjun
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (03) : 517 - 521
  • [7] Synthesis and properties of 3-acyl-γ-pyrones, a novel class of flavones and chromones
    Ganguly, AK
    Kaur, S
    Mahata, PK
    Biswas, D
    Pramanik, BN
    Chan, TM
    [J]. TETRAHEDRON LETTERS, 2005, 46 (23) : 4119 - 4121
  • [8] Pd/C in Propylene Carbonate: A Sustainable Catalyst-Solvent System for the Carbonylative Suzuki-Miyaura Cross-Coupling Using N-Formylsaccharin as a CO Surrogate
    Gautam, Prashant
    Gupta, Rashi
    Bhanage, Bhalchandra M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (24) : 3431 - 3437
  • [9] Pd/C catalyzed phenoxycarbonylation using N-formylsaccharin as a CO surrogate in propylene carbonate, a sustainable solvent
    Gautam, Prashant
    Kathe, Prasad
    Bhanage, Bhalchandra M.
    [J]. GREEN CHEMISTRY, 2017, 19 (03) : 823 - 830
  • [10] Separation/recycling methods for homogeneous transition metal catalysts in continuous flow
    Gursel, Iris Vural
    Nol, Timothy
    Wang, Qi
    Hessel, Volker
    [J]. GREEN CHEMISTRY, 2015, 17 (04) : 2012 - 2026