Suzuki-Miyaura Reactions Catalyzed by C2-Symmetric Pd-Multi-Dentate N-Heterocyclic Carbene Complexes

被引:13
|
作者
Jiang, Lan [1 ,2 ]
Shan, Fengjun [2 ]
Li, Zhengning [2 ]
Zhao, Defeng [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Dalian Univ, Coll Environm & Chem Engn, Dalian 116622, Peoples R China
关键词
imidazolium salt; N-heterocyclic carbene; palladium; Suzuki-Miyaura coupling; catalysis; CROSS-COUPLING REACTIONS; ARYL CHLORIDES; PALLADIUM(II) COMPLEXES; HIGHLY EFFICIENT; ATOM-EFFICIENT; HECK; NHC; LIGANDS; BROMIDES; HALIDES;
D O I
10.3390/molecules171012121
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Suzuki-Miyaura coupling reactions are promoted by Pd complexes ligated with C-2-symmetric multi-dentate N-heterocyclic carbenes derived in situ from Pd(OAc)(2) and imidazolium salts. Good to excellent yields were obtained for aryl bromides as substrates. Turnover numbers of up to 10(5) could be achieved with 5 x 10(-4) mol% of Pd(OAc)(2)/1 x 10(-3) mol% NHC precatalyst in 24 h.
引用
收藏
页码:12121 / 12139
页数:19
相关论文
共 50 条
  • [21] Complexes LNi(Cp)X with alkylamino-substituted N-heterocyclic carbene ligands (L) and their catalytic activity in the Suzuki-Miyaura reaction
    Chesnokov, V. V.
    Shevchenko, M. A.
    Soliev, S. B.
    Tafeenko, V. A.
    Chernyshev, V. M.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (07) : 1281 - 1289
  • [22] N-Heterocyclic Carbene/Pd(II)/1-Methylimidazole Complex Catalyzed Suzuki-Miyaura Coupling Reaction of Aryl Chlorides in Water
    Zhou, Xia-Xia
    Shao, Li-Xiong
    SYNTHESIS-STUTTGART, 2011, (19): : 3138 - 3142
  • [23] Sulfonated N-Heterocyclic Carbenes for Pd-Catalyzed Sonogashira and Suzuki-Miyaura Coupling in Aqueous Solvents
    Roy, Sutapa
    Plenio, Herbert
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 1014 - 1022
  • [24] NHC-Pd(II)-Im (NHC = N-heterocyclic carbene; Im=1-methylimidazole) complexes as efficient catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides
    Tang, Yi-Qiang
    Lu, Jian-Mei
    Shao, Li-Xiong
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (23) : 3741 - 3744
  • [25] Amino acid-derived N-heterocyclic carbene palladium complexes for aqueous phase Suzuki-Miyaura couplings
    Steeples, Elliot
    Kelling, Alexandra
    Schilde, Uwe
    Esposito, Davide
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (06) : 4922 - 4930
  • [26] A novel ditopic ring-expanded N-heterocyclic carbene ligand-assisted Suzuki-Miyaura coupling reaction in aqueous media
    Karaca, Emine Ozge
    Akkoc, Mitat
    Tahir, Muhammad Nawaz
    Arici, Cengiz
    Imik, Fatma
    Gurbuz, Nevin
    Yasar, Sedat
    Ozdemir, Ismail
    TETRAHEDRON LETTERS, 2017, 58 (36) : 3529 - 3532
  • [27] N-heterocyclic carbenes: III. N-heterocyclic carbene ligands based on abietane in Suzuki-Miyaura reaction
    V. A. Glushkov
    M. S. Valieva
    O. A. Maiorova
    E. V. Baigacheva
    A. A. Gorbunov
    Russian Journal of Organic Chemistry, 2011, 47 : 230 - 235
  • [28] Structure-activity relationship of N-heterocyclic carbene-Pd(II)-imidazole complexes in Suzuki-Miyaura coupling between 4-methoxyphenyl chloride and phenylboronic acid
    Lv, Huan
    Zhu, Lei
    Tang, Yi-Qiang
    Lu, Jian-Mei
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (01) : 27 - 31
  • [29] C,N-Palladacycles Containing N-Heterocyclic Carbene and Azido Ligands - Effective Catalysts for Suzuki-Miyaura Cross-Coupling Reactions
    Kim, Yong-Joo
    Lee, Jung-Hyun
    Kim, Taejung
    Ham, Jungyeob
    Zheng, Zhen Nu
    Lee, Soon W.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (36) : 6011 - 6017
  • [30] Pd-PEPPSI-Type Expanded Ring N-Heterocyclic Carbene Complexes: Synthesis, Characterization, and Catalytic Activity in Suzuki-Miyaura Cross Coupling
    Dunsford, Jay J.
    Cavell, Kingsley J.
    ORGANOMETALLICS, 2014, 33 (11) : 2902 - 2905