Synthesis of Aryl(di)azinylmethanes and Bis(di)azinylmethanes via Transition-Metal-Catalyzed Cross-Coupling Reactions

Johan De Houwer; Bert U. W. Maes

doi:10.1055/s-0034-1379025

Synthesis, Table of Contents

Synthesis 2014; 46(19): 2533-2550
DOI: 10.1055/s-0034-1379025

review

Synthesis of Aryl(di)azinylmethanes and Bis(di)azinylmethanes via Transition-Metal-Catalyzed Cross-Coupling Reactions

Johan De Houwer

Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium Fax: +32(3)2653233 Email: bert.maes@uantwerpen.be

,

Bert U. W. Maes*

Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium Fax: +32(3)2653233 Email: bert.maes@uantwerpen.be

› Author Affiliations

Abstract

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Abstract

Aryl(di)azinyl- and bis(di)azinylmethane motifs are important as they are found in a number of pharmaceuticals and their precursors. An exhaustive overview of transition metal-catalyzed cross-coupling reactions for their synthesis has been provided.

1 Introduction

2 Reaction of (Di)azinyl (Pseudo)halides with Benzyl Organometallic Reagents

2.1 Organozinc Reagents – Negishi Reaction

2.2 Organoindium Reagents

2.3 Organoaluminum Reagents

2.4 Organotin Reagents – Migita–Kosugi–Stille Reaction

2.5 Organoboron Reagents – Suzuki–Miyaura Reaction

2.6 (Di)azinyl Methyl Thioether Reagents

3 Reaction of (Di)azinyl Organometallic Reagents with Benzyl (Pseudo)halides

3.1 Organomagnesium Reagents – Kumada Reaction

3.2 Organoaluminum Reagents

3.3 Organoboron Reagents – Suzuki–Miyaura Reaction

4 Reaction of (Di)azinylmethyl Halides with Aryl Organometallic Reagents

4.1 Organoboron Reagents – Suzuki–Miyaura Reaction

5 Reaction of Methyl(di)azine Reagents with Aryl Halides

5.1 Pre-activation of Methyl(di)azines

5.2 In Situ Pre-activation of Methyl(di)azines

5.3 Direct Arylation of Methyl(di)azines

6 Reaction of (Di)azine N-Oxides with Benzyl (Pseudo)halides

7 Conclusion

Key words

heterocycles - transition metals - cross-coupling - palladium - nickel

Full Text

References

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