Abstract

A wide range of methodologies for the preparation of organic azides has been reported in the literature for many decades, due to their interest as building blocks for different transformations and their applications in biology as well as in materials science. More recently, with the spread of the use of transition metal-catalyzed reactions, new perspectives have also materialized in azidation processes, especially concerning the azidation of C–H bonds and direct difunctionalization of multiple carbon-carbon bonds. In this review, special emphasis will be placed on reactions involving substrates bearing a leaving group, hydroazidation reactions and azidation reactions that proceed with the formation of more than one bond. Further reactions for the preparation of allyl and vinyl azides as well as for azidations involving the opening of a ring complete the classification of the material.

Highlights

  • Organic azides show a multifaceted interest in various scientific fields such as chemistry, medicinal chemistry, biology, and material science

  • This review focuses on the new transition metal catalyzed procedures to install the azido group on organic reagent, highlighting applicability, substrate scopes, and mechanisms of the reaction conditions

  • This review is an overview of the procedures based on the use of transition metal catalysts to achieve azido products

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Summary

Introduction

Organic azides show a multifaceted interest in various scientific fields such as chemistry, medicinal chemistry, biology, and material science. Both carbon-carbon and carbon-heteroatom bonds are achievable by avoiding the synthetic steps necessary for the pre-functionalization of the starting materials, considerably reducing the amount of waste materials [37,38,39,40,41,42,43,44,45,46] The interest toward these strategies has grown with the development of transition metal studies in organic synthesis since their use in catalytic quantities is often essential to promote reactions of this type. Procedures to perform allylic azide, hydroazidation processes, and azidations involving ring opening complete the review

Azidation of Substrates Bearing a Leaving Group
Azidation of C-H Bonds
Azidation Involving the Formation of More Than One Bond
Diazidation
Other Preparation of Allylic Azides
Hydroazidation Reactions
Azidation Involving Ring-Opening
Conclusions
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