Highly efficient phosphine-free Suzuki aryl couplings mediated by an in situ generated Pd(OAc)2/metformin complex in green media

被引:32
作者
Alizadeh, A. [1 ,2 ]
Khodaei, M. M. [1 ,2 ]
Kordestani, D. [1 ]
Beygzadeh, M. [1 ]
机构
[1] Razi Univ, Dept Chem, Kermanshah 67149, Iran
[2] Razi Univ, Nanosci & Nanotechnol Res Ctr, Kermanshah 67149, Iran
关键词
Suzuki-Miyaura coupling; Palladium; Biguanide; Catalysis; Organosuperbases; N-HETEROCYCLIC CARBENE; PALLADIUM NANOPARTICLES; AEROBIC CONDITIONS; CATALYST; LIGAND; CHLORIDES; WATER; HALIDES;
D O I
10.1016/j.tetlet.2012.11.031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An in situ generated complex of palladium(II) and a biguanide, namely metformin, was found to be a highly efficient homogeneous catalyst for the phosphine-free Suzuki-Miyaura reaction. Significant rate acceleration of the palladium-catalyzed coupling was observed when a 1:1 mixture of ethanol/water was employed as the reaction solvent. Using this protocol, a variety of aryl halides (Cl, Br, I) were subjected to reaction with various arylboronic acids and the products were obtained in good to excellent yields under mild reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:291 / 294
页数:4
相关论文
共 29 条
  • [1] PEG350-based di-(2-pyridyl)methylamine as a ligand in the Pd-catalyzed water Suzuki-Miyaura reaction of aryl chlorides
    Adidou, Oluissam
    Goux-Henry, Catherine
    Safi, Mohamed
    Soufiaoui, Mohamed
    Framery, Eric
    [J]. TETRAHEDRON LETTERS, 2008, 49 (50) : 7217 - 7219
  • [2] Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles
    Botella, L
    Nájera, C
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 663 (1-2) : 46 - 57
  • [3] Selected patented cross-coupling reaction technologies
    Corbet, Jean-Pierre
    Mignani, Gerard
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2651 - 2710
  • [4] A single-step procedure for the preparation of palladium nanoparticles and a phosphine-functionalized support as catalyst for Suzuki cross-coupling reactions
    Costa, Natalia J. S.
    Kiyohara, Pedro K.
    Monteiro, Adriano L.
    Coppel, Yannick
    Philippot, Karine
    Rossi, Liane M.
    [J]. JOURNAL OF CATALYSIS, 2010, 276 (02) : 382 - 389
  • [5] Triphenylphosphine chalcogenides as efficient ligands for room temperature palladium(II)-catalyzed Suzuki-Miyaura reaction
    Das, Pankaj
    Bora, Utpal
    Tairai, Archana
    Sharma, Chandan
    [J]. TETRAHEDRON LETTERS, 2010, 51 (11) : 1479 - 1482
  • [6] Pd colloid grafted mesoporous silica and its extraordinarily high catalytic activity for Mizoroki-Heck reactions
    Feng, Yingjun
    Li, Liang
    Li, Yongsheng
    Zhao, Wenru
    Gu, Jinlou
    Shi, Jianlin
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 322 (1-2) : 50 - 54
  • [7] Recyclable palladium-catalyzed Sonogashira-Hagihara coupling of aryl halides using 2-aminophenyl diphenylphosphinite ligand in neat water under copper-free condition
    Firouzabadi, Habib
    Iranpoor, Nasser
    Gholinejad, Mohammad
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 321 (1-2) : 110 - 116
  • [8] Simple pyridylmethylamines: efficient and robust N,N-ligands for Suzuki-Miyaura coupling reactions
    Gunawan, Maria-Agatha
    Qiao, Chunjing
    Abrunhosa-Thomas, Isabelle
    Puget, Bertrand
    Roblin, Jean-Philippe
    Prim, Damien
    Troin, Yves
    [J]. TETRAHEDRON LETTERS, 2010, 51 (41) : 5392 - 5394
  • [9] The air-stable and highly efficient P, N-chelated palladium(II) complexes as catalysts for the Suzuki cross-coupling reaction at room temperature
    Guo, MP
    Jian, FF
    He, R
    [J]. TETRAHEDRON LETTERS, 2006, 47 (12) : 2033 - 2036
  • [10] Application of dimeric orthopalladated complex in Suzuki-Miyaura cross coupling reaction under microwave irradiation and conventional heating
    Hajipour, Abdol R.
    Karami, Kazem
    Pirisedigh, Azadeh
    [J]. INORGANICA CHIMICA ACTA, 2011, 370 (01) : 531 - 535