Literature DB >> 34071240

Preparation and Synthetic Application of Naproxen-Containing Diaryliodonium Salts.

Jun Zhou1, Zhiyuan Bao2, Panpan Wu1, Chao Chen2,3.   

Abstract

The synthesis of naproxen-containing diaryliodonium salts has been realized from naproxen methyl ester and ArI(OH)OTs activated by trimethylsilyl trifluoromethanesulfonate (TMSOTf) in a solvent mixture comprising dichloromethane and 2,2,2-trifluoroethanol (TFE). Those iodonium salts have been successfully used in the functionalization of an aromatic ring of naproxen methyl ester, including fluorination, iodination, alkynylation, arylation, thiophenolation, and amination and esterification reactions. Moreover, further hydrolysis of the obtained 5-iodo-naproxen methyl ester afforded 5-iodo-naproxen.

Entities:  

Keywords:  Koser’s reagent; diaryliodonium salts; functionalization; naproxen; naproxen methyl ester

Year:  2021        PMID： 34071240     DOI： 10.3390/molecules26113240

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  20 in total

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Authors:  Peter J. Stang; Viktor V. Zhdankin
Journal:  Chem Rev       Date:  1996-05-09       Impact factor: 60.622

2.  Facile synthesis of Koser's reagent and derivatives from iodine or aryl iodides.

Authors:  Eleanor A Merritt; Vânia M T Carneiro; Luiz F Silva; Berit Olofsson
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3.  Metal-free arylation of oxygen nucleophiles with diaryliodonium salts.

Authors:  Nazli Jalalian; Tue B Petersen; Berit Olofsson
Journal:  Chemistry       Date:  2012-09-27       Impact factor: 5.236

4.  Structure-based discovery of the novel antiviral properties of naproxen against the nucleoprotein of influenza A virus.

Authors:  Nathalie Lejal; Bogdan Tarus; Edwige Bouguyon; Sylvie Chenavas; Nicolas Bertho; Bernard Delmas; Rob W H Ruigrok; Carmelo Di Primo; Anny Slama-Schwok
Journal:  Antimicrob Agents Chemother       Date:  2013-03-04       Impact factor: 5.191

5.  High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides.

Authors:  Marcin Bielawski; Berit Olofsson
Journal:  Chem Commun (Camb)       Date:  2007-03-20       Impact factor: 6.222

6.  In vitro activities of iodonium salts against oral and dental anaerobes.

Authors:  Ellie J C Goldstein; Diane M Citron; Yumi Warren; C Vreni Merriam; Kerin Tyrrell; Helen Fernandez; Ukkiramapandian Radhakrishnan; Peter J Stang; Georg Conrads
Journal:  Antimicrob Agents Chemother       Date:  2004-07       Impact factor: 5.191

7.  Copper(II)-catalyzed three-component cascade annulation of diaryliodoniums, nitriles, and alkynes: a regioselective synthesis of multiply substituted quinolines.

Authors:  Yong Wang; Chao Chen; Jing Peng; Ming Li
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-09       Impact factor: 15.336

8.  Pd-catalyzed divergent trifluoroethylation and arylation of arylboronic acids by aryl(2,2,2-trifluoroethyl)iodonium triflates.

Authors:  Jing Yang; Qiu-Yan Han; Cheng-Long Zhao; Tao Dong; Zhi-Yuan Hou; Hua-Li Qin; Cheng-Pan Zhang
Journal:  Org Biomol Chem       Date:  2016-08-10       Impact factor: 3.876

9.  β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)-H bonds using a palladium catalyst.

Authors:  Jing Peng; Chao Chen; Chanjuan Xi
Journal:  Chem Sci       Date:  2015-11-11       Impact factor: 9.825

Review 10.  Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer.

Authors:  Anamitra Chatterjee; Burkhard König
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-27       Impact factor: 15.336
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