Synthesis 2020; 52(13): 1874-1896
DOI: 10.1055/s-0039-1690858
short review
© Georg Thieme Verlag Stuttgart · New York

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

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Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russian Federation   eMail: i.balova@spbu.ru
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This study was supported by the Russian Science Foundation (19-73-10077).
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Publikationsverlauf

Received: 20. Dezember 2019

Accepted after revision: 26. Februar 2020

Publikationsdatum:
14. April 2020 (online)


Abstract

Copper-catalyzed azide–alkyne cycloaddition is a useful tool for the synthesis of both 1,2,3-triazoles and 5-iodo-1H-1,2,3-triazoles starting from either terminal alkynes or iodoalkynes. 5-Iodotriazoles have been recognized as very useful building blocks for the synthesis of diverse 1,4,5-trisubstituted 1,2,3-triazoles. Synthetic application of 5-iodo-1,2,3-triazoles through the creation of a new C–C, C–heteroatom, or C–D(T) bond along with the application areas of both iodotriazoles and products of their modification including radiolabeled compounds are discussed.

1 Introduction

2 Synthetic Approaches to 5-Iodo-1H-1,2,3-triazoles

3 5-Iodotriazoles in C–C Bond Formation

3.1 Intermolecular C–C Cross-Coupling

3.2 Intramolecular Cross-Coupling: Direct Arylation and C–I/C–I Homocoupling­

3.3 Other Transformations

4 5-Iodotriazoles in Radiolabeling, Halogen Exchange, and Heterocoupling Reactions

5 Summary