Literature DB >> 25614295

Dinuclear copper intermediates in copper(I)-catalyzed azide-alkyne cycloaddition directly observed by electrospray ionization mass spectrometry.

Claudio Iacobucci1, Samantha Reale, Jean-François Gal, Francesco De Angelis.   

Abstract

The mechanism of the CuAAC reaction has been investigated by electrospray ionization mass spectrometry (ESI-MS) using a combination of the neutral reactant approach and the ion-tagging strategy. Under these conditions, for the first time, putative dinuclear copper intermediates were fished out and characterized by ESI(+)-MS/MS. New insight into the CuAAC reaction mechanisms is provided and a catalytic cycle is proposed.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CuAAC reaction; click chemistry; dicopper complexes; mass spectrometry; reactive intermediates

Year:  2015        PMID： 25614295     DOI： 10.1002/anie.201410301

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Tripodal Amine Ligands for Accelerating Cu-Catalyzed Azide-Alkyne Cycloaddition: Efficiency and Stability against Oxidation and Dissociation.

Authors:  Zhiling Zhu; Haoqing Chen; Siheng Li; Xunmo Yang; Eric Bittner; Chengzhi Cai
Journal:  Catal Sci Technol       Date:  2017-04-26       Impact factor: 6.119

2.  Understanding the mechanism and regioselectivity of the copper(i) catalyzed [3 + 2] cycloaddition reaction between azide and alkyne: a systematic DFT study.

Authors:  Hicham Ben El Ayouchia; Lahoucine Bahsis; Hafid Anane; Luis R Domingo; Salah-Eddine Stiriba
Journal:  RSC Adv       Date:  2018-02-16       Impact factor: 4.036

3.  Mechanistic study of CBT-Cys click reaction and its application for identifying bioactive N-terminal cysteine peptides in amniotic fluid.

Authors:  Zhen Zheng; Peiyao Chen; Gongyu Li; Yunxia Zhu; Zhonghua Shi; Yufeng Luo; Chun Zhao; Ziyi Fu; Xianwei Cui; Chenbo Ji; Fuqiang Wang; Guangming Huang; Gaolin Liang
Journal:  Chem Sci       Date:  2016-08-11       Impact factor: 9.825

4.  FAD roles in glucose catalytic oxidation studied by multiphase flow of extractive electrospray ionization (MF-EESI) mass spectrometry.

Authors:  Yan Wang; Min Sun; Jinping Qiao; Jin Ouyang; Na Na
Journal:  Chem Sci       Date:  2017-10-27       Impact factor: 9.825

5.  DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C-N cross-coupling and the origin of ring-opening of 2H-azirines.

Authors:  Fan Yu; Zhaoman Zhou; Jiajia Song; Yanying Zhao
Journal:  RSC Adv       Date:  2021-01-13       Impact factor: 3.361

6.  Cu(ii)-alginate-based superporous hydrogel catalyst for click chemistry azide-alkyne cycloaddition type reactions in water.

Authors:  Lahoucine Bahsis; El-Houssaine Ablouh; Hafid Anane; Moha Taourirte; Miguel Julve; Salah-Eddine Stiriba
Journal:  RSC Adv       Date:  2020-09-03       Impact factor: 4.036

7.  Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) by Functionalized NHC-Based Polynuclear Catalysts: Scope and Mechanistic Insights.

Authors:  Miguel González-Lainez; Miguel Gallegos; Julen Munarriz; Ramón Azpiroz; Vincenzo Passarelli; M Victoria Jiménez; Jesús J Pérez-Torrente
Journal:  Organometallics       Date:  2022-07-15       Impact factor: 3.837
  7 in total

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