Literature DB >> 21336351

Facile synthesis of 4-vinyl- and 4-fluorovinyl-1,2,3-triazoles via bifunctional "click-olefination" reagents.

Rakesh Kumar1, Padmanava Pradhan, Barbara Zajc.   

Abstract

Modular synthesis of vinyl and fluorovinyl triazoles can be achieved from bifunctional propargyl and fluoropropargyl sulfones by Cu-catalyzed azide-alkyne ligation and Julia-Kocienski olefination. Competitive click reactions of the protio and fluoropropargyl sulfones show higher reactivity of the latter, and a preliminary DFT analysis was performed.

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Year:  2011        PMID： 21336351      PMCID： PMC3337081          DOI： 10.1039/c0cc05083k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  25 in total

1.  Mechanism of the ligand-free CuI-catalyzed azide-alkyne cycloaddition reaction.

Authors:  Valentin O Rodionov; Valery V Fokin; M G Finn
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-08       Impact factor: 15.336

2.  The smiles rearrangement and the julia-kocienski olefination reaction.

Authors:  Krzysztof Plesniak; Andrzej Zarecki; Jerzy Wicha
Journal:  Top Curr Chem       Date:  2007

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.  High-yield synthesis of fluorinated benzothiazolyl sulfones: general synthons for fluoro-julia olefinations.

Authors:  Arun K Ghosh; Barbara Zajc
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

5.  Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

Authors:  Fahmi Himo; Timothy Lovell; Robert Hilgraf; Vsevolod V Rostovtsev; Louis Noodleman; K Barry Sharpless; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

6.  Julia Olefination as a General Route to Phenyl (alpha-Fluoro)vinyl Sulfones.

Authors:  Maggie He; Arun K Ghosh; Barbara Zajc
Journal:  Synlett       Date:  2008-04-01       Impact factor: 2.454

7.  Toward the synthesis of benzothiazolyl fluoroaminosulfones.

Authors:  Charlène Calata; Emmanuel Pfund; Thierry Lequeux
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

8.  Fluoro-Julia olefination as a mild, high-yielding route to alpha-fluoro acrylonitriles.

Authors:  Maria del Solar; Arun K Ghosh; Barbara Zajc
Journal:  J Org Chem       Date:  2008-10-08       Impact factor: 4.354

9.  A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems.

Authors:  Nicholas J Agard; Jennifer A Prescher; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

10.  Synthesis of Fluoroolefins via Julia-Kocienski Olefination.

Authors:  Barbara Zajc; Rakesh Kumar
Journal:  Synthesis (Stuttg)       Date:  2010       Impact factor: 3.157
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  7 in total

1.  Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks.

Authors:  Wei Wei; Rama Kanwar Khangarot; Lothar Stahl; Cristina Veresmortean; Padmanava Pradhan; Lijia Yang; Barbara Zajc
Journal:  Org Lett       Date:  2018-06-01       Impact factor: 6.005

2.  Expedient synthesis of α-substituted fluoroethenes.

Authors:  Samir K Mandal; Arun K Ghosh; Rakesh Kumar; Barbara Zajc
Journal:  Org Biomol Chem       Date:  2012-02-20       Impact factor: 3.876

3.  E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents.

Authors:  Rakesh Kumar; Govindra Singh; Louis J Todaro; Lijia Yang; Barbara Zajc
Journal:  Org Biomol Chem       Date:  2015-02-07       Impact factor: 3.876

4.  Stereoselective synthesis of conjugated fluoro enynes.

Authors:  Rakesh Kumar; Barbara Zajc
Journal:  J Org Chem       Date:  2012-09-24       Impact factor: 4.354

5.  Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia-Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape.

Authors:  Shaibal Banerjee; Saikat Sinha; Padmanava Pradhan; Alessio Caruso; Daniel Liebowitz; Damon Parrish; Miriam Rossi; Barbara Zajc
Journal:  J Org Chem       Date:  2016-03-22       Impact factor: 4.354

6.  Highly stereoselective nickel-catalyzed difluoroalkylation of aryl ketones to tetrasubstituted monofluoroalkenes and quaternary alkyl difluorides.

Authors:  Chao Li; Yi-Xuan Cao; Ruo-Xing Jin; Kang-Jie Bian; Zi-Yang Qin; Quan Lan; Xi-Sheng Wang
Journal:  Chem Sci       Date:  2019-08-20       Impact factor: 9.825

7.  Synthesis of regiospecifically fluorinated conjugated dienamides.

Authors:  Mohammad Chowdhury; Samir K Mandal; Shaibal Banerjee; Barbara Zajc
Journal:  Molecules       Date:  2014-04-10       Impact factor: 4.411
  7 in total

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