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
来源：
MOLECULES | 2012年 / 17卷 / 10期
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
  • [41] Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand
    Song, C
    Ma, YD
    Chai, Q
    Ma, CQ
    Jiang, W
    Andrus, MB
    TETRAHEDRON, 2005, 61 (31) : 7438 - 7446
  • [42] Palladium catalyst coordinated in knitting N-heterocyclic carbene porous polymers for efficient Suzuki-Miyaura coupling reactions
    Xu, Shujun
    Song, Kunpeng
    Li, Tao
    Tan, Bien
    JOURNAL OF MATERIALS CHEMISTRY A, 2015, 3 (03) : 1272 - 1278
  • [43] Facile Suzuki-Miyaura cross coupling using ferrocene tethered N-heterocyclic carbene-Pd complex anchored on cellulose
    Kale, Dolly
    Rashinkar, Gajanan
    Kumbhar, Arjun
    Salunkhe, Rajashri
    REACTIVE & FUNCTIONAL POLYMERS, 2017, 116 : 9 - 16
  • [44] Abnormal N-Heterocyclic Carbene Promoted Suzuki-Miyaura Coupling Reaction: A Comparative Study
    Xu, Xiangya
    Xu, Baochang
    Li, Yongxin
    Hong, Soon Hyeok
    ORGANOMETALLICS, 2010, 29 (23) : 6343 - 6349
  • [45] A magnetically separable palladium catalyst containing a bulky N-heterocyclic carbene ligand for the Suzuki-Miyaura reaction
    Wang, Z.
    Yu, Y.
    Zhang, Y. X.
    Li, S. Z.
    Qian, H.
    Lin, Z. Y.
    GREEN CHEMISTRY, 2015, 17 (01) : 413 - 420
  • [46] Cycloheptyl substituted N-heterocyclic carbene PEPPSI-type palladium complexes with different N-coordinated ligands: Involvement in Suzuki-Miyaura reaction
    Karatas, Mert Olgun
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2019, 899
  • [47] Protocol for Palladium/N-Heterocyclic Carbene-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
    Lei, Peng
    Li, Guangchen
    Ling, Yun
    An, Jie
    Nolan, Steven P.
    Szostak, Michal
    SYNTHESIS-STUTTGART, 2021, 53 (04): : 682 - 687
  • [48] Palladium(II)-N-heterocyclic carbene complex derived from proline towards Suzuki-Miyaura coupling reaction in water at room temperature
    Tang, Yi-Qiang
    Lv, Huan
    Lu, Jian-Mei
    Shao, Li-Xiong
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (13) : 2576 - 2579
  • [49] In situ Generation of Efficient Palladium N-heterocyclic Carbene Catalysts Using Benzimidazolium Salts for the Suzuki-Miyaura Cross-coupling Reaction
    Akkoc, Senem
    Gok, Yetkin
    Ilhan, Ilhan Ozer
    Kayser, Veysel
    CURRENT ORGANIC SYNTHESIS, 2016, 13 (05) : 761 - 766
  • [50] Insights into the Suzuki-Miyaura Reaction Catalyzed by Novel Pd-Carbene Complexes. Are Palladium-Tetra- carbene Entities the Key Active Species?
    De Tovar, Jonathan
    Rataboul, Franck
    Djakovitch, Laurent
    CHEMCATCHEM, 2020, 12 (22) : 5797 - 5808
12345