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
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 41期
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
  • [21] Nickel-catalyzed cross-couplings of organosillicon reagents with unactivated secondary alkyl bromides
    Powell, DA
    Fu, GC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) : 7788 - 7789
  • [22] Nickel-catalyzed cross-couplings of organosilicon reagents with unactivated secondary alkyl bromides
    1600, American Chemical Society, Columbus, United States (126):
  • [23] Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides
    Gu, Jun
    Qiu, Canbin
    Lu, Wenbin
    Qian, Qun
    Lin, Kunhua
    Gong, Hegui
    SYNTHESIS-STUTTGART, 2017, 49 (08): : 1867 - 1873
  • [24] Palladium- and Nickel-Catalyzed Amination of Aryl Fluorosulfonates
    Hanley, Patrick S.
    Clark, Thomas P.
    Krasovskiy, Arkady L.
    Ober, Matthias S.
    O'Brien, John P.
    Staton, Tina S.
    ACS CATALYSIS, 2016, 6 (06): : 3515 - 3519
  • [25] Palladium- and nickel-catalyzed intramolecular cyanoboration of alkynes
    Suginome, M
    Yamamoto, A
    Murakami, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) : 6358 - 6359
  • [26] Palladium-catalyzed alkoxycarbonylation of unactivated alkyl bromides
    Sargent, Brendon
    Alexanian, Erik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [27] Nickel- and Cobalt-Catalyzed Direct Alkylation of Azoles with N-Tosylhydrazones Bearing Unactivated Alkyl Groups
    Yao, Tomoyuki
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) : 775 - 779
  • [28] Palladium- and nickel-catalyzed intramolecular cyanoboration of alkynes
    Suginome, M. (suginome@sbchem.kyoto-u.ac.jp), 1600, American Chemical Society (125):
  • [29] Cobalt(I)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides
    Verma, Piyush Kumar
    Prasad, K. Sujit
    Varghese, Dominic
    Geetharani, K.
    ORGANIC LETTERS, 2020, 22 (04) : 1431 - 1436
  • [30] Nickel-Catalyzed Direct Sulfonylation of Styrenes and Unactivated Aliphatic Alkenes with Sulfonyl Chlorides
    Rao, Wei-Hao
    Li, Ying-Ge
    Jiang, Li-Li
    Gao, Chang
    Wang, Yi-Zhuo
    Liu, Jia-Fan
    Zhou, Fu-Yu
    Zou, Guo-Dong
    Cao, Xinhua
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (14): : 9755 - 9768
12345