Palladium- and Nickel-Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides

被引:83
|
作者
Yao, Tomoyuki [1 ]
Hirano, Koji [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
alkylation; azoles; C-H activation; nickel; palladium; C-H BOND; CROSS-COUPLING REACTIONS; GACL3-CATALYZED ORTHO-ETHYNYLATION; DIRECT ARYLATION; DIRECT ALKYNYLATION; CARBON-HYDROGEN; HIGHLY EFFICIENT; SUZUKI REACTIONS; ALKENYLATION; COPPER;
D O I
10.1002/chem.201001631
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Long-ing alkyl chain: The catalytic direct C-H alkylation of azoles with unactivated alkyl bromides and chlorides is described. A palladium catalyst enables the alkylation of oxazoles, whereas a nickel one shows unique activity for thiazole. The catalyses allow a straightforward access to azole motifs bearing long, functional alkyl side chains. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:12307 / 12311
页数:5
相关论文
共 50 条
  • [31] Nickel-catalyzed C-H alkylation of indoles with unactivated alkyl chlorides: evidence of a Ni(i)/Ni(iii) pathway
    Pandey, Dilip K.
    Ankade, Shidheshwar B.
    Ali, Abad
    Vinod, C. P.
    Punji, Benudhar
    CHEMICAL SCIENCE, 2019, 10 (41) : 9493 - 9500
  • [32] Nickel-Catalyzed Direct Cross-Coupling of Unactivated Aryl Fluorides with Aryl Bromides
    Ren, Jing-Ao
    Na, Jin-He
    Gui, Chao
    Miao, Chengping
    Chu, Xue-Qiang
    Ma, Mengtao
    Xu, Hao
    Zhou, Xiaocong
    Shen, Zhi-Liang
    ORGANIC LETTERS, 2023, 25 (29) : 5525 - 5529
  • [33] Recent advances in palladium- and nickel-catalyzed coupling reactions
    Fu, Gregory C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [34] Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides
    Everson, Daniel A.
    Jones, Brittany A.
    Weix, Daniel J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (14) : 6146 - 6159
  • [35] A practical nickel-catalyzed reductive alkylation of amidophenyl bromides
    Liu, Xuge
    Yang, Zhilin
    Li, Ya-Min
    Yang, Fan
    Feng, Liang
    Wang, Nengzhong
    Ma, Debiao
    Chang, Kwen-Jen
    Shen, Yuehai
    TETRAHEDRON, 2014, 70 (50) : 9522 - 9529
  • [36] Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates
    Ackermann, Lutz
    Sandmann, Rene
    Song, Weifeng
    ORGANIC LETTERS, 2011, 13 (07) : 1784 - 1786
  • [37] DFT study on mechanism of nickel-catalyzed decarbonylative reductive alkylation of aroyl fluorides with alkyl bromides
    Liu, Lijuan
    Shang, Zhenfeng
    Li, Ruifang
    Xu, Xiufang
    TETRAHEDRON LETTERS, 2024, 152
  • [38] Palladium-catalyzed Negishi cross-coupling reactions of unactivated alkyl iodides, bromides, chlorides, and tosylates
    Zhou, JR
    Fu, GC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) : 12527 - 12530
  • [39] Nickel-Catalyzed Formal Aminocarbonylation of Unactivated Alkyl Iodides with Isocyanides
    Huang, Wenyi
    Wang, Yun
    Weng, Yangyang
    Shrestha, Mohini
    Qu, Jingping
    Chen, Yifeng
    ORGANIC LETTERS, 2020, 22 (08) : 3245 - 3250
  • [40] Nickel-Catalyzed Remote Arylation of Alkenyl Aldehydes Initiated by Radical Alkylation with Tertiary α-Carbonyl Alkyl Bromides
    Jin, Weiwei
    Zhou, Yulu
    Zhao, Ying
    Ma, Qianqian
    Kong, Lichun
    Zhu, Gangguo
    ORGANIC LETTERS, 2018, 20 (05) : 1435 - 1438