Literature DB >> 20849130

Carboxylic acid-promoted copper(I)-catalyzed azide-alkyne cycloaddition.

Changwei Shao1, Xinyan Wang, Jimin Xu, Jichen Zhao, Qun Zhang, Yuefei Hu.   

Abstract

In this article, we proved that all three key steps in the catalytic cycle of CuAAC can proceed in the presence of carboxylic acids and the latter two steps can be promoted significantly by carboxylic acids. Benzoic acid showed the best promotion activity, and the acids with strong chelating ability to Cu(I) ion could not serve for this purpose. Thus, the first carboxylic acid-promoted highly efficient CuAAC was established.

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Year:  2010        PMID： 20849130     DOI： 10.1021/jo101495k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  14 in total

1.  α-Azido ketones. Part 7: synthesis of 1,4-disubstituted triazoles by the "click" reaction of various terminal acetylenes with phenacyl azides or α-azidobenzo(hetera)cyclanones.

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2.  Aminopeptidase P Mediated Targeting for Breast Tissue Specific Conjugate Delivery.

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Journal:  Bioconjug Chem       Date:  2016-08-19       Impact factor: 4.774

3.  Synthesis of deuterated 1,2,3-triazoles.

Authors:  Hari K Akula; Mahesh K Lakshman
Journal:  J Org Chem       Date:  2012-09-27       Impact factor: 4.354

4.  Preparation of Enantiomerically Pure Perfluorobutanesulfinamide and Its Application to the Asymmetric Synthesis of α-Amino Acids.

Authors:  Apiwat Wangweerawong; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal:  J Org Chem       Date:  2016-02-04       Impact factor: 4.354

5.  One-pot three component synthesis of 5-allyl-1,2,3-triazoles using copper(i) acetylides.

Authors:  Parigi Raghavendar Reddy; Lianji Cui; Jae-Sang Ryu
Journal:  RSC Adv       Date:  2018-01-12       Impact factor: 4.036

6.  Gold(I) and Palladium(II) Complexes of 1,3,4-Trisubstituted 1,2,3-Triazol-5-ylidene "Click" Carbenes: Systematic Study of the Electronic and Steric Influence on Catalytic Activity.

Authors:  James R Wright; Paul C Young; Nigel T Lucas; Ai-Lan Lee; James D Crowley
Journal:  Organometallics       Date:  2013-11-21       Impact factor: 3.876

7.  Sequential decarboxylative azide-alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles.

Authors:  Kuppusamy Bharathimohan; Thanasekaran Ponpandian; A Jafar Ahamed; Nattamai Bhuvanesh
Journal:  Beilstein J Org Chem       Date:  2014-12-17       Impact factor: 2.883

8.  Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production.

Authors:  Sándor B Otvös; Adám Georgiádes; István M Mándity; Lóránd Kiss; Ferenc Fülöp
Journal:  Beilstein J Org Chem       Date:  2013-07-29       Impact factor: 2.883

9.  Symmetric molecules with 1,4-triazole moieties as potent inhibitors of tumour-associated lactate dehydrogenase-A.

Authors:  Abdul-Malek S Altamimi; Ahmed M Alafeefy; Agnese Balode; Igor Vozny; Aleksandrs Pustenko; Mohey Eldin El Shikh; Fatmah A S Alasmary; Sherif A Abdel-Gawad; Raivis Žalubovskis
Journal:  J Enzyme Inhib Med Chem       Date:  2018-12       Impact factor: 5.051

10.  A Versatile Strategy for the Synthesis of 4,5-Dihydroxy-2,3-Pentanedione (DPD) and Related Compounds as Potential Modulators of Bacterial Quorum Sensing.

Authors:  Silvia Stotani; Viviana Gatta; Federico Medda; Mohan Padmanaban; Anna Karawajczyk; Päivi Tammela; Fabrizio Giordanetto; Dimitrios Tzalis; Simona Collina
Journal:  Molecules       Date:  2018-10-06       Impact factor: 4.411
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