Synthesis of symmetrical and unsymmetrical tellurides via silver catalysis

被引:11
|
作者
Goldani, Bruna [1 ]
do Sacramento, Manoela [1 ]
Lenardao, Eder J. [1 ]
Schumacher, Ricardo F. [1 ]
Barcellos, Thiago [2 ]
Alves, Diego [1 ]
机构
[1] Univ Fed Pelotas, UFPel, Lab Sintese Organ Limpa, LASOL,CCQFA, POB 354, BR-96010900 Pelotas, RS, Brazil
[2] Univ Caxias Do Sul, Lab Biotechnol Nat & Synthet Prod, Caxias Do Sul, RS, Brazil
关键词
CROSS-COUPLING REACTIONS; ARYL BORONIC ACIDS; C-H BOND; ORGANOTELLURIUM COMPOUNDS; DIARYL CHALCOGENIDES; ARYLBORONIC ACIDS; TE BOND; ANTIOXIDANT ACTIVITY; ORGANOBORONIC ACIDS; TERMINAL ALKYNES;
D O I
10.1039/c8nj01998c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe here a simple and efficient methodology for the cross-coupling reaction of diaryl ditellurides with aryl boronic acids catalyzed by AgNO3. The general applicability and wide substrate scope make this an interesting method for the synthesis of a series of symmetrical and unsymmetrical diaryl tellurides. This silver-catalyzed protocol tolerates a variety of diaryl ditellurides as well as aryl boronic acids by using only 10 mol% of AgNO3 to provide the desired products in high yields. The reaction mechanism was proposed after high resolution mass spectrometry analysis and the active (PhTe)(2)Ag-III intermediate could be detected.
引用
收藏
页码:15603 / 15609
页数:7
相关论文
共 50 条
  • [1] Transition-Metal-Free Synthesis of Unsymmetrical Diaryl Tellurides via SH2 Reaction of Aryl Radicals on Tellurium
    Yamamoto, Yuki
    Sato, Fumiya
    Chen, Qiqi
    Kodama, Shintaro
    Nomoto, Akihiro
    Ogawa, Akiya
    MOLECULES, 2022, 27 (03):
  • [2] Synthesis of α,β-unsaturated aryl esters via Heck reaction of unsymmetrical aryl tellurides
    Stefani, Helio A.
    Pena, Jesus M.
    Gueogjian, Kemilla
    Petragnani, Nicola
    Vaz, Boniek G.
    Eberlin, Marcos N.
    TETRAHEDRON LETTERS, 2009, 50 (40) : 5589 - 5595
  • [3] Approach to the Synthesis of Unsymmetrical/Symmetrical Maleimides via Desulfitative Arylation at Different Temperatures
    Abbasnia, Masoumeh
    Sheykhan, Mehdi
    Ghaffari, Tahereh
    Safari, Elham
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (18) : 11688 - 11698
  • [4] One-Pot Synthesis of Symmetrical and Unsymmetrical Diarylmethanes via Diborylmethane
    Endo, Kohei
    Ishioka, Takafumi
    Ohkubo, Takahiro
    Shibata, Takanori
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) : 7223 - 7231
  • [5] A Cascade Synthesis of Unsymmetrical Furanized Triarylmethanes via Gold Self-Relay Catalysis
    Rao, Qian
    Zhang, Yan
    Gu, Xin-Yu
    Liu, Yin-Ping
    Jiang, Bo
    Hao, Wen-Juan
    CATALYSTS, 2023, 13 (07)
  • [6] Metal-Free Synthesis of Unsymmetrical Aryl Selenides and Tellurides via Visible Light-Driven Activation of Arylazo Sulfones
    Liu, Junjie
    Tian, Miaomiao
    Li, Yuxuan
    Shan, Xiwen
    Li, Ankun
    Lu, Kui
    Fagnoni, Maurizio
    Protti, Stefano
    Zhao, Xia
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (47) : 7358 - 7367
  • [7] Synthesis of Unsymmetrical Diaryl Tellurides Under Mechanical Ball Milling in Room Temperature
    Roy, Anup
    Panja, Subir
    Basu, Pradipta Kumar
    Kundu, Debasish
    CURRENT ORGANIC CHEMISTRY, 2024, 28 (04) : 319 - 324
  • [8] Catalyst free one-pot synthesis of symmetrical diaryl tellurides with Te0/KOH
    Zhang, Shaozhong
    Karra, Kranthi
    Koe, Adam
    Jin, Jin
    TETRAHEDRON LETTERS, 2013, 54 (20) : 2452 - 2454
  • [9] Selective Suzuki- Miyaura Monocouplings with Symmetrical Dibromoarenes and Aryl Ditriflates for the One- Pot Synthesis of Unsymmetrical Triaryls
    Minard, Corinne
    Palacio, Carole
    Cariou, Kevin
    Dodd, Robert H.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (14) : 2942 - 2955
  • [10] Symmetrical disulfide synthesis via nickel-catalysis using potassium sulfide as sulfur source
    Soleiman-Beigi, Mohammad
    Arzehgar, Zeinab
    MONATSHEFTE FUR CHEMIE, 2016, 147 (10): : 1759 - 1763