Literature DB >> 22368306

Fast dye salts provide fast access to azidoarene synthons in multi-step one-pot tandem click transformations.

James T Fletcher1, Jacquelline E Reilly.   

Abstract

This study examined whether commercially available diazonium salts could be used as efficient aromatic azide precursors in one-pot multi-step click transformations. Seven different diazonium salts, including Fast Red RC, Fast Blue B, Fast Corinth V and Variamine Blue B were surveyed under aqueous click reaction conditions of CuSO(4)/Na ascorbate catalyst with 1:1 t-BuOH:H(2)O solvent. Two-step tandem reactions with terminal alkyne and diyne co-reactants led to 1,2,3-triazole products in 66%-88% yields, while three-step tandem reactions with trimethylsilyl-protected alkyne and diyne co-reactants led to 1,2,3-triazole products in 61%-78% yields.

Entities:  

Year:  2011        PMID: 22368306      PMCID: PMC3285242          DOI: 10.1016/j.tetlet.2011.08.069

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  12 in total

Review 1.  Cu-catalyzed azide-alkyne cycloaddition.

Authors:  Morten Meldal; Christian Wenzel Tornøe
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

2.  One-pot procedure for diazo transfer and azide-alkyne cycloaddition: triazole linkages from amines.

Authors:  Henning S G Beckmann; Valentin Wittmann
Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

3.  A versatile new monomer family: functionalized 4-vinyl-1,2,3-triazoles via click chemistry.

Authors:  Raymond J Thibault; Kenichi Takizawa; Peter Lowenheilm; Brett Helms; Justin L Mynar; Jean M J Fréchet; Craig J Hawker
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

4.  A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction.

Authors:  Prasad Appukkuttan; Wim Dehaen; Valery V Fokin; Erik Van der Eycken
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

5.  One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides.

Authors:  Alina K Feldman; Benoît Colasson; Valery V Fokin
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

6.  Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.

Authors:  Christian W Tornøe; Caspar Christensen; Morten Meldal
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

7.  Tandem catalysis: from alkynoic acids and aryl iodides to 1,2,3-triazoles in one pot.

Authors:  Andrej Kolarovič; Michael Schnürch; Marko D Mihovilovic
Journal:  J Org Chem       Date:  2011-03-10       Impact factor: 4.354

8.  Organic azides: an exploding diversity of a unique class of compounds.

Authors:  Stefan Bräse; Carmen Gil; Kerstin Knepper; Viktor Zimmermann
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

9.  Ab initio study of the SN1Ar and SN2Ar reactions of benzenediazonium ion with water. On the conception of "unimolecular dediazoniation" in solvolysis reactions.

Authors:  Zhengyu Wu; Rainer Glaser
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419

10.  Efficient conversion of aromatic amines into azides: a one-pot synthesis of triazole linkages.

Authors:  Karine Barral; Adam D Moorhouse; John E Moses
Journal:  Org Lett       Date:  2007-03-29       Impact factor: 6.005

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  1 in total

1.  Tandem synthesis of 1-formyl-1,2,3-triazoles.

Authors:  James T Fletcher; Joseph A Christensen; Eric M Villa
Journal:  Tetrahedron Lett       Date:  2017-10-13       Impact factor: 2.415

  1 in total

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