Chalcogen-Bonding Catalysis with Telluronium Cations

被引：73
|
作者：
Weiss, Robin [1 ]
Aubert, Emmanuel [2 ]
Pale, Patrick [1 ]
Mamane, Victor [1 ]
机构：
[1] Univ Strasbourg, LASYROC, UMR 7177, 1 Rue Blaise Pascal, F-67000 Strasbourg, France
[2] Univ Lorraine, CRM2, BP 70239,Blvd Aiguillettes, F-54506 Vandoeuvre Les Nancy, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 35期
关键词：
chalcogen bonding; Lewis acids; non-covalent interactions; organocatalysis; tellurium; N-ARYL IMINES; ORGANOTELLURIUM COMPOUNDS; TELLURIUM; HALOGEN; SALTS; XPS;
D O I：
10.1002/anie.202105482
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chalcogen bonding results from non-covalent interactions occurring between electrodeficient chalcogen atoms and Lewis bases. Among the chalcogens, tellurium is the strongest Lewis acid, but Te-based compounds are scarcely used as organocatalysts. For the first time, telluronium cations demonstrated impressive catalytic properties at low loadings in three benchmark reactions: the Friedel-Crafts bromination of anisole, the bromolactonization of omega-unsaturated carboxylic acids and the aza-Diels-Alder between Danishefsky's diene and imines. The ability of telluronium cations to interact with a Lewis base through chalcogen bonding was demonstrated on the basis of multi-nuclear (O-17, P-31, and Te-125) NMR analysis and DFT calculations.
引用
收藏
页码：19281 / 19286
页数：6
相关论文
共 50 条
  • [21] Theoretical study on cooperative interplay between anion-π and chalcogen-bonding interactions
    Samimi, Heshmat Allah
    Esrafili, Mehdi D.
    Mohammadian-Sabet, Fariba
    Haddadi, Hedayat
    MOLECULAR PHYSICS, 2015, 113 (12) : 1442 - 1450
  • [22] Chalcogen bonding in the solid-state structures of 1,3-bis(benzimidazoliumyl)benzene-based chalcogen-bonding donors
    Steinke, Tim
    Engelage, Elric
    Huber, Stefan M.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2023, 79 : 26 - +
  • [23] Multistate Redox-Switchable Ion Transport Using Chalcogen-Bonding Anionophores
    Docker, Andrew
    Johnson, Toby G.
    Kuhn, Heike
    Zhang, Zongyao
    Langton, Matthew J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (04) : 2661 - 2668
  • [24] Formation of chalcogen-bonding interactions and their role in the trans-trans conformation of thiourea
    Inoue, Takumi
    Morita, Nami
    Amijima, Yui
    Sakai, Rika
    Hamada, Shohei
    Nakamura, Seikou
    Kobayashi, Yusuke
    Furuta, Takumi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (26) : 5301 - 5305
  • [25] Dual Chalcogen-Bonding Interaction for High-Performance Filterless Narrowband Organic Photodetectors
    Kim, Hyeong-Ju
    Kim, Bongsu
    Yun, Sungyoung
    Yun, Dong-Jin
    Choi, Taejin
    Lee, Sangjun
    Minami, Daiki
    Heo, Chul-Joon
    Lim, Juhyung
    Shibuya, Hiromasa
    Lim, Younhee
    Shin, Jisoo
    Hong, Hyerim
    Park, Jeong-Il
    Fang, Feifei
    Seo, Hwijoung
    Yi, Jeoungin
    Park, Sangho
    Lee, Hyun Hwi
    Park, Kyung-Bae
    SMALL, 2024, 20 (37)
  • [26] Chalcogen-Chalcogen Bonding Catalysis Enables Assembly of Discrete Molecules
    Wang, Wei
    Zhu, Haofu
    Liu, Shuya
    Zhao, Zhiguo
    Zhang, Liang
    Hao, Jingcheng
    Wang, Yao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (23) : 9175 - 9179
  • [27] Chalcogen bonding in synthesis, catalysis and design of materials
    Mahmudov, Kamran T.
    Kopylovich, Maximilian N.
    Guedes da Silva, M. Fatima C.
    Pombeiro, Armando J. L.
    DALTON TRANSACTIONS, 2017, 46 (31) : 10121 - 10138
  • [28] Chalcogen Bonding Catalysis with Phosphonium Chalcogenide (PCH)
    Zhao, Zhiguo
    Wang, Yao
    ACCOUNTS OF CHEMICAL RESEARCH, 2023, : 608 - 621
  • [29] Chalcogen Bonding Catalysis: Tellurium, the Last Frontier?
    Pale, Patrick
    Mamane, Victor
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (69)
  • [30] Reversible Self-Assembly of Supramolecular Vesicles and Nanofibers Driven by Chalcogen-Bonding Interactions
    Chen, Liang
    Xiang, Jun
    Zhao, Yue
    Yan, Qiang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (23) : 7079 - 7082
12345