Literature DB >> 25420599

Synthesis of azoimidazolium dyes with nitrous oxide.

Alexander G Tskhovrebov1, Lara C E Naested, Euro Solari, Rosario Scopelliti, Kay Severin.   

Abstract

A new method for the synthesis of industrially important azoimidazolium dyes is presented. The procedure is based on a reagent which is rarely used in the context of synthetic organic chemistry: nitrous oxide ("laughing gas"). N2O is first coupled to N-heterocyclic carbenes. Subsequent reaction with aromatic compounds through an AlCl3-induced C-H activation process provides azoimidazolium dyes in good yields.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; azo coupling; carbenes; dyes; nitrous oxide

Mesh：

Substances：

Year:  2014        PMID： 25420599     DOI： 10.1002/anie.201410067

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  5 in total

1.  Synthesis of aminyl biradicals by base-induced Csp3-Csp3 coupling of cationic azo dyes.

Authors:  Yizhu Liu; Paul Varava; Alberto Fabrizio; Léonard Y M Eymann; Alexander G Tskhovrebov; Ophélie Marie Planes; Euro Solari; Farzaneh Fadaei-Tirani; Rosario Scopelliti; Andrzej Sienkiewicz; Clémence Corminboeuf; Kay Severin
Journal:  Chem Sci       Date:  2019-05-09       Impact factor: 9.825

2.  Crystal structure of 2-[(E)-2-(4-bromo-phen-yl)diazen-1-yl]-4,5-bis-(4-meth-oxy-phen-yl)-1H-imidazole: the first example of a structurally characterized tri-aryl-azo-imid-azole.

Authors:  Ayalew Temesgen; Alexander G Tskhovrebov; Anna V Vologzhanina; Tuan A Le; Victor N Khrustalev
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2021-02-26

3.  Azulenesulfonium Salts: Accessible, Stable, and Versatile Reagents for Cross-Coupling.

Authors:  Paul Cowper; Yu Jin; Michael D Turton; Gabriele Kociok-Köhn; Simon E Lewis
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-14       Impact factor: 15.336

4.  Azulene Functionalization by Iron-Mediated Addition to a Cyclohexadiene Scaffold.

Authors:  Petter Dunås; Lloyd C Murfin; Oscar J Nilsson; Nicolas Jame; Simon E Lewis; Nina Kann
Journal:  J Org Chem       Date:  2020-10-21       Impact factor: 4.354

5.  Unprecedented Coordination-Induced Bright Red Emission from Group 12 Metal-Bound Triarylazoimidazoles.

Authors:  Artyom A Astafiev; Olga V Repina; Boris S Tupertsev; Alexey A Nazarov; Maria R Gonchar; Anna V Vologzhanina; Valentine G Nenajdenko; Andreii S Kritchenkov; Victor N Khrustalev; Victor N Nadtochenko; Alexander G Tskhovrebov
Journal:  Molecules       Date:  2021-03-20       Impact factor: 4.411
  5 in total

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