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Synthesis 2007(11): 1589-1620  
DOI: 10.1055/s-2007-966071
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Click Chemistry - What’s in a Name? Triazole Synthesis and Beyond

María Victoria Gil*a, María José Arévaloa, Óscar Lópezb
a Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Extremadura, 06071 Badajoz, Spain
Fax: +34(924)271149; e-Mail: vgil@unex.es;
b Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, 41012 Seville, Spain
Further Information

Publication History

Received 21 February 2007
Publication Date:
11 May 2007 (online)

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Abstract

The environmentally amiable route to carbon-heteroatom bond formation, described by Sharpless as ‘click chemistry’, has become known as a fast, efficient, and reliable approach to the synthesis of novel compounds with desired functionalities. Readily available starting materials must be used in this methodology and they should be essentially inert to most biological and organic conditions, including water and molecular oxygen. In this review, we cover reactions included in this label such as cycloadditions, nucleophilic ring-opening reactions of strained cycles, and amide synthesis, as well as their applications in organic synthesis, molecular biology, macromolecular chemistry and materials science.

  • 1 Introduction

  • 2 Click Synthesis of Epoxides and Aziridines

  • 3 Nucleophilic Opening of Strained Rings: Epoxides and Aziridines

  • 4 Huisgen 1,3-Dipolar Cycloadditions

  • 4.1 Supramolecular Click Chemistry

  • 4.2 Liquid Crystals

  • 4.3 Self-Assembled Monolayers

  • 4.4 Multicomponent Reactions

  • 4.5 Creating Drug Candidates under Click Conditions

  • 4.6 Click Chemistry with Peptides and Proteins

  • 4.7 DNA as Participant in Click Reactions

  • 5 Concluding Remarks

Key words

drug research - supramolecular chemistry - Huisgen cycloadditions­ - triazole - aziridine opening - epoxide opening