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Literature DB >> 20825167

Transition-metal-free catalytic synthesis of 1,5-diaryl-1,2,3-triazoles.

Sen W Kwok¹, Joseph R Fotsing, Rebecca J Fraser, Valentin O Rodionov, Valery V Fokin.

Abstract

1,5-Diarylsubstituted 1,2,3-triazoles are formed in high yield from aryl azides and terminal alkynes in DMSO in the presence of catalytic tetraalkylammonium hydroxide. The reaction is experimentally simple, does not require a transition-metal catalyst, and is not sensitive to atmospheric oxygen and moisture.

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20825167 PMCID： PMC2946857 DOI： 10.1021/ol101568d

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

10 in total

1. A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.

Authors: Vsevolod V Rostovtsev; Luke G Green; Valery V Fokin; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2002-07-15 Impact factor: 15.336

2. Trimethylsilyl-directed 1,3-dipolar cycloaddition reactions in the solid-phase synthesis of 1,2,3-triazoles.

Authors: Steven J Coats; Jeffrey S Link; Diane Gauthier; Dennis J Hlasta
Journal: Org Lett Date: 2005-04-14 Impact factor: 6.005

3. Ruthenium-catalyzed cycloaddition of alkynes and organic azides.

Authors: Li Zhang; Xinguo Chen; Peng Xue; Herman H Y Sun; Ian D Williams; K Barry Sharpless; Valery V Fokin; Guochen Jia
Journal: J Am Chem Soc Date: 2005-11-23 Impact factor: 15.419

4. Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base.

Authors: Teruhiko Ishikawa; Tomohiro Mizuta; Kumiko Hagiwara; Toshiaki Aikawa; Takayuki Kudo; Seiki Saito
Journal: J Org Chem Date: 2003-05-02 Impact factor: 4.354

5. 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

6. Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited.

Authors: Antoni Krasiński; Valery V Fokin; K Barry Sharpless
Journal: Org Lett Date: 2004-04-15 Impact factor: 6.005

7. Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism.

Authors: Brant C Boren; Sridhar Narayan; Lars K Rasmussen; Li Zhang; Haitao Zhao; Zhenyang Lin; Guochen Jia; Valery V Fokin
Journal: J Am Chem Soc Date: 2008-06-21 Impact factor: 15.419

Review 8. The growing applications of click chemistry.

Authors: John E Moses; Adam D Moorhouse
Journal: Chem Soc Rev Date: 2007-05-03 Impact factor: 54.564

9. Clicking polymers: a straightforward approach to novel macromolecular architectures.

Authors: David Fournier; Richard Hoogenboom; Ulrich S Schubert
Journal: Chem Soc Rev Date: 2007-05-03 Impact factor: 54.564

10. Ruthenium-catalyzed cycloaddition of aryl azides and alkynes.

Authors: Lars Kyhn Rasmussen; Brant C Boren; Valery V Fokin
Journal: Org Lett Date: 2007-12-01 Impact factor: 6.005

10 in total

18 in total

1. Antimicrobial 1,3,4-trisubstituted-1,2,3-triazolium salts.

Authors: James T Fletcher; Jill M Sobczyk; Sarah C Gwazdacz; Aaron J Blanck
Journal: Bioorg Med Chem Lett Date: 2018-09-10 Impact factor: 2.823

Review 2. Transition metal-free one-pot synthesis of nitrogen-containing heterocycles.

Authors: Simpal Kumari; Dharma Kishore; Sarvesh Paliwal; Rajani Chauhan; Jaya Dwivedi; Aakanksha Mishra
Journal: Mol Divers Date: 2015-06-09 Impact factor: 2.943

Review 3. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors: Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal: Chem Rev Date: 2013-01-10 Impact factor: 60.622

4. Synthesis of Highly Stable 1,3-Diaryl-1H-1,2,3-triazol-5-ylidenes and their Applications in Ruthenium-Catalyzed Olefin Metathesis.

Authors: Jean Bouffard; Benjamin K Keitz; Ralf Tonner; Vincent Lavallo; Gregorio Guisado-Barrios; Gernot Frenking; Robert H Grubbs; Guy Bertrand
Journal: Organometallics Date: 2011-03-09 Impact factor: 3.876

5. Inhibition of the FAD containing ER oxidoreductin 1 (Ero1) protein by EN-460 as a strategy for treatment of multiple myeloma.

Authors: Karen E Hayes; Paratchata Batsomboon; Wei-Chih Chen; Brennan D Johnson; Andreas Becker; Steven Eschrich; Yan Yang; Aaron R Robart; Gregory B Dudley; Werner J Geldenhuys; Lori A Hazlehurst
Journal: Bioorg Med Chem Date: 2019-02-10 Impact factor: 3.641

6. Integrated and passive 1,2,3-triazolyl groups in fluorescent indicators for zinc(II) ions: thermodynamic and kinetic evaluations.

Authors: J Tyler Simmons; John R Allen; Deborah R Morris; Ronald J Clark; Cathy W Levenson; Michael W Davidson; Lei Zhu
Journal: Inorg Chem Date: 2013-04-26 Impact factor: 5.165