Mesomeric betaine - N-heterocyclic carbene interconversions of 1,2,4-triazolium-phenolates. Sulfur, selenium, and borane adduct formation

被引:33
|
作者
Liu, Ming [1 ]
Nieger, Martin [2 ]
Schmidt, Andreas [1 ]
机构
[1] Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany
[2] Univ Helsinki, Dept Chem, Inorgan Chem Lab, FIN-00014 Helsinki, Finland
关键词
NUCLEOPHILIC CARBENES; COMPLEXES; YLIDES; CHEMISTRY; DECARBOXYLATION; IMIDAZOLIUM; PRECURSORS; GENERATION; CONVERSION; INDAZOLE;
D O I
10.1039/c4cc08032g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The conjugated mesomeric betaines 2-(1-phenyl-4H-1,2,4-triazolium-4-yl)phenolates are masked N-heterocyclic carbenes of 1,2,4-triazole which can be trapped as thiones and selenones. Reaction with triethylborane and triphenylborane resulted in the formation of first representatives of a new zwitterionic heterocyclic ring system, benzo[e]1,2,4-triazolo[3,4-c][1,4,2]oxazaborinium-4-ide, as a formal trapping product of an anionic N-heterocyclic carbene.
引用
收藏
页码:477 / 479
页数:3
相关论文
共 35 条
  • [31] One pot tandem dehydrogenative cross-coupling of primary and secondary alcohols by ruthenium amido-functionalized 1,2,4-triazole derived N-heterocyclic carbene complexes
    Kumar, Anuj
    Ta, Sabyasachi
    Nettem, Chandrasekhar
    Tanski, Joseph M.
    Rajaraman, Gopalan
    Ghosh, Prasenjit
    RSC ADVANCES, 2022, 12 (45) : 28961 - 28984
  • [32] Reactions of 1-Alkyl-3-phenylbenzimidazolium Salts with Ag2O: The Formation of a Ring-Opening Formamide Derivative and a Ag Complex with an N-heterocyclic Carbene Ligand
    Sakaguchi, Satoshi
    Higashino, Takashi
    Tasaki, Yudai
    Ichihara, Ryo
    Yajima, Tatsuo
    INORGANICS, 2025, 13 (01)
  • [33] N-Heterocyclic Carbene-Catalyzed in situ Activation of Alkynyl Acids for C-S Bond Formation: Access to Imidazo[2,1-b][1,3]thiazinones
    Sun, Kewen
    Jin, Shiyi
    Zhu, Jindong
    Zhang, Xinmiao
    Gao, Maoyu
    Zhang, Wanqi
    Lu, Tao
    Du, Ding
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (23) : 4515 - 4522
  • [34] Design and Synthesis of Camphor-derived Chiral [1,2,4]Triazolo[4,3-a]tetrahydroquinoline N-Heterocyclic Carbene Precursors by Pd-Catalyzed Coupling Reactions of Aryl Hydrazides with a Pyridyl Triflate Derivative
    Chen, Liang-An
    Wang, Chuan-Fei
    Lin, Ming-Gui
    Zhang, Jin-Long
    Huang, Pei-Qiang
    Wang, Ai-E
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (04) : 294 - 298
  • [35] Sequential one-pot and three-component reactions of an N-heterocyclic carbene to form 4-(1,2,4-triazol-5-ylidene)pyrrolidine-2,5-diones: a tandem umpolung/annulation sequence via deoxy-Breslow intermediates
    Matsuoka, Shin-ichi
    Tochigi, Yusuke
    Takagi, Koji
    Suzuki, Masato
    TETRAHEDRON, 2012, 68 (47) : 9836 - 9841