Palladium-catalyzed Cross-coupling of 2-Benzo[b]thiophene or 2-Benzo[b]furan Aluminum with Heteroaryl or Alkynyl Bromides for the Synthesis of 2-Hetroaryl or Alkynyl Benzo[b]thiophene or Benzo[b]furan Derivatives

被引：3
作者：
Liang, Meng [1 ,2 ]
Pu, Jiaxia [1 ,2 ]
Jia, Xiaoying [1 ,2 ]
Han, Lirong [1 ,2 ]
Li, Qinghan [1 ,2 ,3 ]
机构：
[1] Southwest Minzu Univ, Coll Chem & Environm, Chengdu 610041, Peoples R China
[2] Southwest Minzu Univ, Coll Chem & Environm, Key Lab Gen Chem Natl Ethn Affairs Commiss, Chengdu 610041, Peoples R China
[3] Southwest Minzu Univ, Coll Chem & Environm, POB 610041, Chengdu, Peoples R China
来源：
LETTERS IN ORGANIC CHEMISTRY | 2024年 / 21卷 / 02期
关键词：
Palladium; 2-benzo[b]thiophene; 2-benzo[b]furan; alkynyl bromide; heteroaryl aluminum; cross-coupling reaction; ONE-POT SYNTHESIS; ELECTROPHILIC CYCLIZATION; RESEARCH PROGRESS; TERMINAL ALKYNES; FUNCTIONALIZATION; NANOPARTICLES; HYDROALKOXYLATION; BENZOTHIOPHENES; BENZOFURANS; ANNULATION;
D O I：
10.2174/1570178620666230821142342
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An alternative method for the synthesis of 2-heteroaryl or alkynyl benzo[b]thiophene or furan derivatives via direct palladium-catalyzed cross-coupling of 2-benzo[b]thiophene or furan aluminum with heteroaryl or alkynyl bromides, respectively, has been successfully developed. This case is remarkable as the same catalytic system could simultaneously produce either 2-substituted benzo[b]thiophene or furan derivatives.
引用
收藏
页码：116 / 123
页数：8
相关论文
共 54 条
  • [1] Indium(III)-Catalyzed Synthesis of Benzo[b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights
    Alonso-Maranon, Lorena
    Montserrat Martinez, M.
    Sarandeses, Luis A.
    Gomez-Bengoa, Enrique
    Perez Sestelo, Jose
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) : 7970 - 7980
  • [2] Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease
    Berger, W.
    De Chandt, M. T. M.
    Cairns, C. B.
    [J]. INTERNATIONAL JOURNAL OF CLINICAL PRACTICE, 2007, 61 (04) : 663 - 676
  • [3] Novel Benzo[b]thiophene Derivatives as New Potential Antidepressants with Rapid Onset of Action
    Berrade, Luis
    Aisa, Barbara
    Ramirez, Maria J.
    Galiano, Silvia
    Guccione, Salvatore
    Moltzau, Lise Roman
    Levy, Finn Olav
    Nicoletti, Ferdinando
    Battaglia, Giuseppe
    Molinaro, Gemma
    Aldana, Ignacio
    Monge, Antonio
    Perez-Silanes, Silvia
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (08) : 3086 - 3090
  • [4] Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: synthesis of benzo[b]thiophene 2,3-oxide
    Boyd, Derek R.
    Sharma, Narain D.
    Brannigan, Ian N.
    Evans, Timothy A.
    Haughey, Simon A.
    McMurray, Brian T.
    Malone, John F.
    McIntyre, Peter B. A.
    Stevenson, Paul J.
    Allen, Christopher C. R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (36) : 7292 - 7304
  • [5] Synthesis of Benzofurans and Indoles from Terminal Alkynes and Iodoaromatics Catalyzed by Recyclable Palladium Nanoparticles Immobilized on Siliceous Mesocellular Foam
    Bruneau, Alexandre
    Gustafson, Karl P. J.
    Yuan, Ning
    Tai, Cheuk-Wai
    Persson, Ingmar
    Zou, Xiaodong
    Baeckvall, Jan-E.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (52) : 12886 - 12891
  • [6] Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines
    Cai, Tao
    Feng, Chengjie
    Shen, Fangqi
    Bian, Kejun
    Wu, Chunlei
    Shen, Runpu
    Gao, Yuzhen
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (04) : 653 - 656
  • [7] Palladium nanoparticles in glycerol: a clear-cut catalyst for one-pot multi-step processes applied in the synthesis of heterocyclic compounds
    Chahdoura, Faouzi
    Mallet-Ladeira, Sonia
    Gomez, Montserrat
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (04): : 312 - 318
  • [8] Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[b]thiophenes
    Colletto, Chiara
    Panigrahi, Adyasha
    Fernandez-Casado, Jaime
    Larrosa, Igor
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (30) : 9638 - 9643
  • [9] Recent advances in the synthesis of raloxifene: A selective estrogen receptor modulator
    Dadiboyena, Sureshbabu
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 51 : 17 - 34
  • [10] One-Pot Synthesis of Amine-Substituted Aryl Sulfides and Benzo[b]thiophene Derivatives
    Duan, Zhongyu
    Ranjit, Sadananda
    Liu, Xiaogang
    [J]. ORGANIC LETTERS, 2010, 12 (10) : 2430 - 2433
123456