New phosphine-functionalized N-heterocyclic carbene ligands for palladium-catalyzed hydroarylation reaction

被引:40
|
作者
Zhong, Jun
Xie, Jian-Hua
Wang, Ai-E
Zhang, Wei
Zhou, Qi-Lin [1 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
bicyclic alkene; functionalized phosphine ligand; hydroarylation; N-heterocyclic carbene; palladium;
D O I
10.1055/s-2006-939077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel triarylphosphine-functionalized imidazolinium salts have been prepared and successfully applied in palladium-catalyzed hydroarylation of bicyclic olefins. Under reductive conditions (HCOOH, Et3N), the complexes generated in situ from imidazolinium salts and Pd(OAc)(2) catalyzed the hydroarylation of bicyclic alkenes with aryl iodides, providing the hydroarylation products with high turnover numbers (TON, up to 1.9.10(5)) and turnover frequencies (TOF, up to 6.3.10(4)).
引用
收藏
页码:1193 / 1196
页数:4
相关论文
共 50 条
  • [1] Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction
    Wang, AE
    Xie, JH
    Wang, LX
    Zhou, QL
    TETRAHEDRON, 2005, 61 (01) : 259 - 266
  • [2] Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands
    Shi, Ji-cheng
    Yang, Pengyu
    Tong, Qingsong
    Jia, Li
    DALTON TRANSACTIONS, 2008, (07) : 938 - 945
  • [3] Potential N-Heterocyclic Carbene Precursors in the Palladium-Catalyzed Heck Reaction
    Demir, Serpil
    Zengin, Rukiye
    Ozdemir, Ismail
    HETEROATOM CHEMISTRY, 2013, 24 (01) : 77 - 83
  • [4] Ruthenium(II) supported by phosphine-functionalized N-heterocyclic carbene ligands as catalysts for the transfer hydrogenation of ketones
    Humphries, Matthew E.
    Pecak, Wiktoria H.
    Hohenboken, Sallie A.
    Alvarado, Samuel R.
    Swenson, Dale C.
    Domski, Gregory J.
    INORGANIC CHEMISTRY COMMUNICATIONS, 2013, 37 : 138 - 143
  • [5] Chelating N-heterocyclic carbene ligands in palladium-catalyzed Heck-type reactions
    Herrmann, WA
    Reisinger, CP
    Spiegler, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 557 (01) : 93 - 96
  • [6] Chelating Bis(N-Heterocyclic Carbene) Palladium-Catalyzed Reactions
    Liu, Ji-Quan
    Gou, Xing-Xing
    Han, Ying-Feng
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2257 - 2276
  • [7] Palladium-catalyzed Heck reaction of aryl bromides in aqueous media using tris(N-heterocyclic carbene) ligands
    Ozdemir, Ismail
    Demir, Serpil
    Cetinkaya, Bekir
    SYNLETT, 2007, (06) : 889 - 892
  • [8] Novel triphenylarsinyl-functionalized N-heterocyclic carbene ligands in palladium-catalyzed C-C coupling reactions
    Stiemke, Frank
    Gjikaj, Mimoza
    Kaufmann, Dieter E.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (01) : 5 - 13
  • [9] A convenient synthesis of phosphine-functionalized N-heterocyclic carbene ligand precursors, structural characterization of their palladium complexes and catalytic application in Suzuki coupling reaction
    Lee, HM
    Chiu, PL
    Zeng, JY
    INORGANICA CHIMICA ACTA, 2004, 357 (14) : 4313 - 4321
  • [10] Direct Arylation Mediated by Palladium Complexes with Rigid Phosphine-Functionalized N-Heterocyclic Carbenes
    Ho, Chien-Chang
    Chatterjee, Sandipan
    Wu, Tzu-Liang
    Chan, Kai-Ting
    Chang, Yu-Wei
    Hsiao, Tsun-Hung
    Lee, Hon Man
    ORGANOMETALLICS, 2009, 28 (09) : 2837 - 2847