A study of the scope and regioselectivity of the ruthenium-catalyzed [3+2]-cycloaddition of azides with internal alkynes

被引：209
|
作者：
Majireck, Max M. [1 ]
Weinreb, Steven M. [1 ]
机构：
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 22期
关键词：
D O I：
10.1021/jo061688m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[3 + 2]-Cycloadditions of alkyl azides with various unsymmetrical internal alkynes in the presence of Cp*RuCl(PPh3)(2) as catalyst in refluxing benzene have been examined, leading to 1,4,5-trisubstituted-1,2,3-triazoles. Whereas alkyl phenyl and dialkyl acetylenes undergo cycloadditions to afford mixtures of regioisomeric 1,2,3-triazoles, acyl-substituted internal alkynes react with complete regioselectivity. In addition, propargyl alcohols and propargyl amines were found to react with azides to afford single regioisomeric products.
引用
收藏
页码：8680 / 8683
页数：4
相关论文
共 50 条
  • [1] Electronic effects of ruthenium-catalyzed [3+2]-cycloaddition of alkynes and azides
    Hou, Duen-Ren
    Kuan, Ting-Chun
    Li, Yu-Kai
    Lee, Richmond
    Huang, Kuo-Wei
    [J]. TETRAHEDRON, 2010, 66 (48) : 9415 - 9420
  • [2] Ruthenium-catalyzed cycloaddition of aryl azides and alkynes
    Rasmussen, Lars Kyhn
    Boren, Brant C.
    Fokin, Valery V.
    [J]. ORGANIC LETTERS, 2007, 9 (26) : 5337 - 5339
  • [3] Ruthenium-catalyzed cycloaddition of alkynes and organic azides
    Zhang, L
    Chen, XG
    Xue, P
    Sun, HHY
    Williams, ID
    Sharpless, KB
    Fokin, VV
    Jia, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 15998 - 15999
  • [4] Prediction of the regioselectivity of the ruthenium-catalyzed [3+2] cycloadditions of benzyl azide with internal alkynes using conceptual DFT indices of reactivity
    Yousfi, Youcef
    Benchouk, Wafaa
    Mekelleche, Sidi Mohamed
    [J]. CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (3) : 118 - 127
  • [5] Prediction of the regioselectivity of the ruthenium-catalyzed [3+2] cycloadditions of benzyl azide with internal alkynes using conceptual DFT indices of reactivity
    Youcef Yousfi
    Wafaa Benchouk
    Sidi Mohamed Mekelleche
    [J]. Chemistry of Heterocyclic Compounds, 2023, 59 : 118 - 127
  • [6] Ruthenium-Catalyzed [3+2] Cycloaddition of 2H-Azirines with Alkynes: Access to Polysubstituted Pyrroles
    Li, Tengfei
    Yan, Hao
    Li, Xincheng
    Wang, Chunxiang
    Wan, Boshun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23): : 12031 - 12037
  • [7] Ruthenium-Catalyzed Hydrocarboxylation of Internal Alkynes
    Jeschke, Janine
    Engelhardt, Tony B.
    Lang, Heinrich
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (08) : 1548 - 1554
  • [8] Mechanistic insight into the ruthenium-catalyzed cycloaddition of enynes with alkynes: A theoretical study
    Liu, Ruiqiu
    Tie, Yunfei
    Zhao, Xiaoyan
    Zhu, Jinjiao
    Zou, Jie
    Liu, Tao
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 875 : 46 - 51
  • [9] Ruthenium-catalyzed hydrosilylation of 1-alkynes with novel regioselectivity
    Kawanami, Y
    Sonoda, Y
    Mori, T
    Yamamoto, K
    [J]. ORGANIC LETTERS, 2002, 4 (17) : 2825 - 2827
  • [10] Ruthenium-catalyzed [2+2+2] cycloaddition of three different alkynes
    Ura, Y
    Sato, Y
    Tsujita, H
    Kondo, T
    Imachi, M
    Mitsudo, TA
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 239 (1-2) : 166 - 171
12345