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
  • [31] Palladium N-Heterocyclic Carbene Catalysts for the Ultrasound-Promoted Suzuki-Miyaura Reaction in Glycerol
    Azua, Arturo
    Mata, Jose A.
    Heymes, Pauline
    Peris, Eduardo
    Lamaty, Frederic
    Martinez, Jean
    Colacino, Evelina
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) : 1107 - 1116
  • [32] On the efficiency of two-coordinate palladium(0) N-heterocyclic carbene complexes in amination and Suzuki-Miyaura reactions of aryl chlorides
    Arentsen, K
    Caddick, S
    Cloke, FGN
    TETRAHEDRON, 2005, 61 (41) : 9710 - 9715
  • [33] A new palladium(II) complex of a functionalized N-heterocyclic carbene: Synthesis, characterization and application in Suzuki-Miyaura cross-coupling reactions
    Linninger, Claudia S.
    Herdtweck, Eberhardt
    Hoffmann, Stephan D.
    Herrmann, Wolfgang A.
    Kuehn, Fritz E.
    JOURNAL OF MOLECULAR STRUCTURE, 2008, 890 (1-3) : 192 - 197
  • [34] Nickel(ii) N-heterocyclic carbene complexes as efficient catalysts for the Suzuki—Miyaura reaction
    S. B. Soliev
    A. V. Astakhov
    D. V. Pasyukov
    V. M. Chernyshev
    Russian Chemical Bulletin, 2020, 69 : 683 - 690
  • [35] Progress in the Heck Reaction and Suzuki Reaction Catalyzed by Pd-N-Heterocyclic Carbene Complexes
    Jiang, Lan
    Li, Zhengning
    Zhao, Defeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (02) : 200 - 210
  • [36] Nickel/N-Heterocyclic Carbene-Catalyzed Suzuki-Miyaura Type Cross-Coupling of Aryl Carbamates
    Ohtsuki, Akimichi
    Yanagisawa, Kousuke
    Furukawa, Takayuki
    Tobisu, Mamoru
    Chatani, Naoto
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) : 9409 - 9414
  • [37] N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling
    Reeves, Emily K.
    Humke, Jenna N.
    Neufeldt, Sharon R.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (18) : 11799 - 11812
  • [38] Palladium(II) Complexes with Small N-Heterocyclic Carbene Ligands as Highly Active Catalysts for the Suzuki-Miyaura Cross-Coupling Reaction
    Szulmanowicz, Michal S.
    Gniewek, Andrzej
    Gil, Wojciech
    Trzeciak, Anna M.
    CHEMCATCHEM, 2013, 5 (05) : 1152 - 1160
  • [39] Immobilization of a Pd(ii)-containing N-heterocyclic carbene ligand on porous organic polymers: efficient and recyclable catalysts for Suzuki-Miyaura reactions
    Lin, Hongwei
    Gao, Xiyue
    Yao, Huan
    Luo, Qionglin
    Xiang, Bailin
    Liu, Cijie
    Ouyang, Yuejun
    Zhou, Nonglin
    Xiang, Dexuan
    CATALYSIS SCIENCE & TECHNOLOGY, 2021, 11 (11) : 3676 - 3680
  • [40] Syntheses of Novel C2-Symmetric Chiral Bidentate Bis(N-heterocyclic carbene) Ligands and Their Molybdenum Complexes
    Anezaki, Satoshi
    Yamaguchi, Yoshitaka
    Asami, Masatoshi
    CHEMISTRY LETTERS, 2010, 39 (04) : 398 - 399