Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aube rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

https://www.chem.ccu.edu.tw/~joyce/referance/ericyang/Coord.%20Chem.%20Rev/Coord.%20Chem.%20Rev.%202004,%20248,%202337-2364.pdf

Copper in cross-coupling reactions: The post-Ullmann chemistry

This Review summarizes the advances in the construction of all-carbon quaternary stereocenters via catalytic enantioselective desymmetrization of prochiral and meso-compounds, highlights the power and potential of this strategy in the total synthesis of natural products and biologically active compounds, and outlines the synthetic opportunities still available.

Catalytic Enantioselective Desymmetrization Reactions to All-Carbon Quaternary Stereocenters.

Seit der Entdeckung der organischen Azide vor uber einhundertvierzig Jahren durch Peter Gries wurde eine Reihe von Synthesen fur diese energiereichen Molekule entwickelt. In letzter Zeit haben sich vollig neue Perspektiven durch Anwendungen in der Peptidchemie, der kombinatorischen Chemie und der Heterocyclensynthese ergeben. Auf dem interdisziplinaren Gebiet zwischen Chemie, Biologie, Medizin und Materialwissenschaften nehmen organische Azide inzwischen einen wichtigen Raum ein. In diesem Aufsatz werden die Grundzuge der Azid-Chemie dargelegt und aktuelle Entwicklungen auf diesem Gebiet beleuchtet. Der Schwerpunkt liegt dabei auf Cycloadditionen (Huisgen-Reaktion), Aza-Ylidchemie und der Synthese von Heterocyclen. Weitere Reaktionen wie die Aza-Wittig-Reaktion, Sundberg-Umlagerung, Staudinger-Ligation, Boyer- und Boyer-Aube-Umlagerung, Curtius-Umlagerung, Schmidt-Umlagerung sowie die Hemetsberger-Umlagerung zeugen von der Vielfaltigkeit moderner Azid-Chemie.

Organische Azide – explodierende Vielfalt bei einer einzigartigen Substanzklasse

Polystyrene-supported hydroxyproline: an insoluble, recyclable organocatalyst for the asymmetric aldol reaction in water

Triarylborane ammonia complexes as ideal precursors for arylzinc reagents in asymmetric catalysis.

Hydro-dediazoniation of diazonium salts using trichlorosilane: new cleavage conditions for the T1 traceless linker

The effects of additives in phenylzinc addition reactions to an aldehyde have been studied using an automated high-throughput screening approach. With 2-bromobenzaldehyde as test substrate and N,N-dibutylnorephedrine (dbne) as chiral ligand, an improvement of 20% ee over the catalyzed reaction in the absence of the additive was observed. The described results enable a novel access towards chiral diarylmethanols using commercially available substrates, reagents and ligands as well as fast, automated techniques.

A High‐Throughput Screening Approach for the Determination of Additive Effects in Organozinc Addition Reactions to Aldehydes

Efficient synthesis of highly substituted diaryl ethers on solid supports using the Ullmann reaction.

Solid supported fluoronitroaryl triazenes as immobilized and convertible Sanger reagents – synthesis and SNAr reactions towards a novel preparation of 1-alkyl-5-nitro-1H-benzotriazoles

Matthias Lormann

Papers

Triarylborane ammonia complexes as ideal precursors for arylzinc reagents in asymmetric catalysis.

Hydro-dediazoniation of diazonium salts using trichlorosilane: new cleavage conditions for the T1 traceless linker

A High‐Throughput Screening Approach for the Determination of Additive Effects in Organozinc Addition Reactions to Aldehydes

Efficient synthesis of highly substituted diaryl ethers on solid supports using the Ullmann reaction.

Solid supported fluoronitroaryl triazenes as immobilized and convertible Sanger reagents – synthesis and SNAr reactions towards a novel preparation of 1-alkyl-5-nitro-1H-benzotriazoles