Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N-Acyl Arylhydrazines

被引:14
作者
Cao, Jun [1 ,3 ]
Chen, Zi-Li [2 ]
Li, Shu-Min [3 ]
Zhu, Gao-Feng [3 ]
Yang, Yuan-Yong [3 ]
Wang, Cong [3 ]
Chen, Wen-Zhang [4 ]
Wang, Jian-Ta [3 ]
Zhang, Ji-Quan [1 ,3 ,4 ]
Tang, Lei [1 ,4 ]
机构
[1] Guizhou Med Univ, State Key Lab Funct & Applicat Med Plants, Guiyang 550014, Peoples R China
[2] Guizhou Med Univ, Affiliated Hosp, Guiyang 550004, Peoples R China
[3] Guizhou Med Univ, Coll Pharm, Guiyang 550025, Peoples R China
[4] Guizhou Med Univ, Guizhou Prov Engn Technol Res Ctr Chem Drug R&D, Guiyang 550004, Peoples R China
关键词
Arylation; Palladium; Benzofurans; Arylhydrazines; Regioselectivity; C-H FUNCTIONALIZATION; BOND FORMATION; DERIVATIVES; INHIBITORS; COMPLEX; OLEFINS; MILD; LEAD;
D O I
10.1002/ejoc.201800374
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.
引用
收藏
页码:2774 / 2779
页数:6
相关论文
共 40 条
  • [1] Development of a Novel Lead that Targets M. tuberculosis Polyketide Synthase 13
    Aggarwal, Anup
    Parai, Maloy K.
    Shetty, Nishant
    Wallis, Deeann
    Woolhiser, Lisa
    Hastings, Courtney
    Dutta, Noton K.
    Galaviz, Stacy
    Dhakal, Ramesh C.
    Shrestha, Rupesh
    Wakabayashi, Shoko
    Walpole, Chris
    Matthews, David
    Floyd, David
    Scullion, Paul
    Riley, Jennifer
    Epemolu, Ola
    Norval, Suzanne
    Snavely, Thomas
    Robertson, Gregory T.
    Rubin, Eric J.
    Ioerger, Thomas R.
    Sirgel, Frik A.
    van der Merwe, Ruben
    van Helden, Paul D.
    Keller, Peter
    Bottger, Erik C.
    Karakousis, Petros C.
    Lenaerts, Anne J.
    Sacchettini, James C.
    [J]. CELL, 2017, 170 (02) : 249 - +
  • [2] [Anonymous], 2008, ANGEW CHEM INT EDIT
  • [3] Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed C-Glycosylation
    Bai, Yaguang
    Kim, Le Mai Hoang
    Liao, Hongze
    Liu, Xue-Wei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17) : 8821 - 8825
  • [4] A Convenient Synthesis of 2-Arylbenzo[b]furans from Aryl Halides and 2-Halophenols by Catalytic One-Pot Cascade Method
    Bosiak, Mariusz Jan
    [J]. ACS CATALYSIS, 2016, 6 (04): : 2429 - 2434
  • [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] Impregnated palladium on magnetite as catalyst for direct arylation of heterocycles
    Cano, Rafael
    Perez, Juana M.
    Ramon, Diego J.
    McGlacken, Gerard P.
    [J]. TETRAHEDRON, 2016, 72 (08) : 1043 - 1050
  • [7] A review on antioxidant potential of bioactive heterocycle benzofuran: Natural and synthetic derivatives
    Chand, Karam
    Rajeshwari
    Hiremathad, Asha
    Singh, Mahak
    Santos, M. Amelia
    Keri, Rangappa S.
    [J]. PHARMACOLOGICAL REPORTS, 2017, 69 (02) : 281 - 295
  • [8] Palladium-Catalyzed Direct Denitrogenative C-3-Arylation of 1H-Indoles with Arylhydrazines using Air as the Oxidant
    Chen, Yongxin
    Guo, Shuaibo
    Li, Kangning
    Qu, Jinpeng
    Yuan, Hua
    Hua, Qiuru
    Chen, Baohua
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) : 711 - 715
  • [9] A novel 18F-labeled pyridyl benzofuran derivative for imaging of β-amyloid plaques in Alzheimer's brains
    Cheng, Yan
    Ono, Masahiro
    Kimura, Hiroyuki
    Kagawa, Shinya
    Nishii, Ryuichi
    Saji, Hideo
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (20) : 6141 - 6144
  • [10] Delord J. Wencel-, 2012, ANGEW CHEM, V124, P13175, DOI DOI 10.1002/ANGE.201205734