N-Arylation of Protected Azamacrocycles

被引：5
|
作者：
Veiga, Alberte X. [1 ]
Arenz, Sven [1 ]
Erdelyi, Mate [1 ]
机构：
[1] Univ Gothenburg, Dept Chem & Mol Biol, S-41296 Gothenburg, Sweden
来源：
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 06期
基金：
瑞典研究理事会;
关键词：
azamacrocycles; N-arylation; C-N coupling; heterocycles; homogeneous catalysis; PALLADIUM-CATALYZED AMINATION; FORMING REDUCTIVE ELIMINATION; CONTRAST AGENTS; ARYL; CYCLEN; SEPARATION; MECHANISM;
D O I：
10.1055/s-0032-1318307
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rapid method for efficient palladium-catalyzed N-arylation of polynitrogenated macrocycles is presented. Its applicability for functionalization of protected azamacrocycles of various sizes with substituted aryl bromides of optional electronic properties is demonstrated. The compatibility of the protocol with common N-protecting schemes as well as the impact of electronic versus steric factors is discussed. Using a commercially available catalytic system and easily available alkoxide or phenoxide base, the method provides moderate to excellent yields of N-arylated azamacrocycles (45-96%).
引用
收藏
页码：777 / 784
页数：8
相关论文
共 50 条
  • [21] The copper-catalyzed N-arylation of indoles
    Antilla, JC
    Klapars, A
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) : 11684 - 11688
  • [22] POLYPYRAZOLES .3. N-ARYLATION OF PYRAZOLES
    CHIRIAC, C
    STOICESC.L
    ZUGRAVES.I
    REVUE ROUMAINE DE CHIMIE, 1969, 14 (10) : 1263 - &
  • [23] Nickel-Catalyzed N-Arylation of Fluoroalkylamines
    McGuire, Ryan T.
    Yadav, Arun A.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (08) : 4080 - 4084
  • [24] N-Arylation of Heterocycles Promoted by Cyclen Derivatives
    Zhang, Bao-Hua
    Shi, Lan-xiang
    Liu, Si-Jie
    Guo, Rui-Xia
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (04) : 1234 - 1239
  • [25] Palladium-Catalyzed N-Arylation of Cyclopropylamines
    Gildner, Peter G.
    DeAngelis, Andrew
    Colacot, Thomas J.
    ORGANIC LETTERS, 2016, 18 (06) : 1442 - 1445
  • [26] Microwave-enhanced copper-catalyzed n-arylation of free and protected amino acids in water
    Rottger, Svenja
    Sjoberg, Per J. R.
    Larhed, Mats
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (02): : 204 - 209
  • [27] Copper-Promoted N-Arylation of the Imidazole Side Chain of Protected Histidine by Using Triarylbismuth Reagents
    Chan, Hwai-Chien
    Bueno, Bianca
    Le Roch, Adrien
    Gagnon, Alexandre
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (53) : 13330 - 13336
  • [28] Concurrent α-Iodination and N-Arylation of Cyclic β-Enaminones
    Chen, Yan
    Ju, Tong
    Wang, Junwei
    Yu, Wenquan
    Du, Yunfei
    Zhao, Kang
    SYNLETT, 2010, (02) : 231 - 234
  • [29] Copper-Catalyzed N-Arylation of Sulfonimidamides
    Azzaro, Stephane
    Desage-El Murr, Marine
    Fensterbank, Louis
    Lacote, Emmanuel
    Malacria, Max
    SYNLETT, 2011, (06) : 849 - 851
  • [30] Recent Progress Concerning the N-Arylation of Indoles
    Oeser, Petr
    Koudelka, Jakub
    Petrenko, Artem
    Tobrman, Tomas
    MOLECULES, 2021, 26 (16):
12345