First Application of an Efficient and Versatile Ligand for Copper-Catalyzed Cross-Coupling Reactions of Vinyl Halides with N-Heterocycles and Phenols

被引:66
作者
Kabir, M. Shahjahan [1 ]
Lorenz, Michael [1 ]
Namjoshi, Ojas A. [1 ]
Cook, James M. [1 ]
机构
[1] Univ Wisconsin, Dept Chem & Biochem, Milwaukee, WI 53201 USA
关键词
ULLMANN-TYPE REACTION; C-N; O-ARYLATION; PALLADIUM; IODIDES; AMIDES; NITROGEN; BROMIDES; ETHERS; THIOLS;
D O I
10.1021/ol9026446
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Pyridin-2-yl-1H-benzoimidazole U is presented as a new, efficient, and versatile bidentate N-donor ligand suitable for the copper-catalyzed formation of vinyl C-N and C-O bonds. This inexpensive and easily prepared ligand facilitates copper-catalyzed cross-coupling reactions of alkenyl bromides and iodides with A heterocycles and phenols to afford the desired cross-coupled products in good to excellent yields with full retention of stereochemistry. This method is particularly noteworthy given its efficiency, that is, mild reaction conditions, low catalyst loading, simplicity, versatility, and exceptional level of functional group tolerance.
引用
收藏
页码:464 / 467
页数:4
相关论文
共 50 条
  • [31] Synthesis of oxygen heterocycles via Pd-catalyzed cross-coupling of unsaturated phenols and vinylic halides or triflates
    Larock, RC
    Yang, H
    Pace, P
    Narayanan, K
    Russell, CE
    Cacchi, S
    Fabrizi, G
    TETRAHEDRON, 1998, 54 (26) : 7343 - 7356
  • [32] 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides
    Qiu, Yatao
    Jia, Weijun
    Yao, Zhiyi
    Wu, Fanhong
    Jiang, Sheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (09) : 1502 - 1510
  • [33] Copper-catalyzed homo- and cross-coupling reactions of terminal alkynes in ethyl lactate
    Wan, Jie-Ping
    Cao, Shuo
    Jing, Yanfeng
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (08) : 631 - 634
  • [34] Scaled-Up Transition-Metal-Catalyzed Cross-Coupling Reactions of Thioether-Substituted N-Heterocycles with Organozinc Reagents
    Metzger, Albrecht
    Melzig, Laurin
    Knochel, Paul
    SYNTHESIS-STUTTGART, 2010, (16): : 2853 - 2858
  • [35] Use of Acylhydrazine- and Acylhydrazone-Type Ligands to Promote CuI-Catalyzed C-N Cross-Coupling Reactions of Aryl Bromides with N-Heterocycles
    Li, Liuyi
    Zhu, Lei
    Chen, Dagui
    Hu, Xuelei
    Wang, Ruihu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (14) : 2692 - 2696
  • [36] Mechanistic Insights into Copper-Catalyzed Sonogashira-Hagihara-Type Cross-Coupling Reactions: Sub-Mol% Catalyst Loadings and Ligand Effects
    Zou, Liang-Hua
    Johansson, Adam Johannes
    Zuidema, Erik
    Bolm, Carsten
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (25) : 8144 - 8152
  • [37] Copper-Catalyzed Cross-Coupling of Nonactivated Secondary Alkyl Halides and Tosylates with Secondary Alkyl Grignard Reagents
    Yang, Chu-Ting
    Zhang, Zhen-Qi
    Liang, Jun
    Liu, Jing-Hui
    Lu, Xiao-Yu
    Chen, Huan-Huan
    Liu, Lei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (27) : 11124 - 11127
  • [38] Copper-catalyzed sp3-sp3 cross-coupling of turbo grignards with benzyl halides
    Petruncio, Greg
    Elahi-Mohassel, Synah
    Girgis, Michael
    Paige, Mikell
    TETRAHEDRON LETTERS, 2021, 86
  • [39] Tandem reactions initiated by copper-catalyzed cross-coupling: A new strategy towards heterocycle synthesis
    Liu, Yunyun
    Wan, Jie-Ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (20) : 6873 - 6894
  • [40] Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions
    Cheval, Nicolas P.
    Hoffmann, Barbara
    Dikova, Anna
    Sirindil, Fatih
    Bertus, Philippe
    Blanc, Aurelien
    Weibel, Jean-Marc
    Pale, Patrick
    TETRAHEDRON, 2018, 74 (50) : 7111 - 7119