Azaheterocyclic Derivatives of ortho-Carborane: Synthetic Strategies and Application Opportunities

Lidiia A. Smyshliaeva; Mikhail V. Varaksin; Valery N. Charushin; Oleg N. Chupakhin

doi:10.1055/s-0039-1690733

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(03): 337-352
DOI: 10.1055/s-0039-1690733

short review

Azaheterocyclic Derivatives of ortho-Carborane: Synthetic Strategies and Application Opportunities

Lidiia A. Smyshliaeva

^aUral Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation

^bI.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation eMail: chupakhin@ios.uran.ru

,

Mikhail V. Varaksin

^aUral Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation

^bI.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation eMail: chupakhin@ios.uran.ru

,

Valery N. Charushin

^aUral Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation

^bI.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation eMail: chupakhin@ios.uran.ru

,

Oleg N. Chupakhin ∗

^aUral Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation

^bI.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation eMail: chupakhin@ios.uran.ru

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Abstract

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Abstract

Azaheterocyclic derivatives of 1,2-dicarba-closo-dodecaborane (ortho-carborane) are known to be of particular interest due to numerous plausible applications, particularly, in medicine, materials science, and advanced technologies. Three principal synthetic strategies resulting in azaheterocyclic carboranes, in which boron-enriched and azaheterocyclic fragments are linked to each other, either directly by means of the C–C bonds or through a short spacer (CH₂, CH₂S, CH₂O, etc.), have been outlined. These synthetic approaches are of general character and can be used both individually and in combination to afford promising organoboron clusters of diverse architectures.

1 Introduction

2 C–C Cross-Coupling Strategies in the Synthesis of Azaheterocyclic Carboranes

3 Carboryne-Based Transformation Strategies

4 Condensation Strategies: Reactions of Decaborane B₁₀H₁₄ with Substituted Acetylenes

5 Conclusion and Outlook

Key words

carboranes - azaheterocycles - cross-coupling reactions - carboryne - decaborane

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Referenzen

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