Special Issue "Click Chemistry"
QuicklinksA special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Synthesis".
Deadline for manuscript submissions: 31 July 2010
Special Issue Editor
Guest Editor
Prof. Dr. Christian Girard
Laboratoire de Pharmacologie Chimique et Génétique, UMR8151, CNRS - U640 INSERM ¨C IFR2769, Ecole Nationale Supérieure de Chimie de Paris, 11 rue Pierre et Marie Curie, 75005 Paris, France
Website: http://www.enscp.fr/labos/umr8151/girard1.html
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Published Papers
Special Issue Information
Click-chemistry is a new way of thinking molecular construction that emerges at the turn of this century. This concept, introduced by K. B. Sharpless, is based on the use of fast and efficient reactions between building blocks that opens the way to quasi-illimited variations in chemical architecture. Click-chemistry permits the construction of highly diversified structures through the use of reactive subunits, that can be joined using nucleophilic and electrophilic substitutions, ring opening reactions, cycloadditions reactions such as the copper (I)-modified Huisgen reaction and the Diels-Alder one, additions to unsaturated bonds, carbonyl chemistry, and so on. The scope of this new way of thinking molecular construction is large and has found many applications in classical organic synthesis, polymers and material sciences, as well as at the biological interface, with biocompatible conditions.
Guest Editor
Submission
Keywords
- click-chemistry
- organic synthesis
- molecular diversity
- methodology
- application
- interfaces with other sciences (pharmaceutical, biological, polymers, materials, etc.)
Planned Papers
Manuscript ID: Molecules-clickchem-20090608-fr-Girard
Title: Automated Synthesis of a 96-Product Sized Library of Triazole Derivatives Using a Solid Phase Supported Copper Catalyst
Type of Paper : Article
Authors: I. Jlalia, C. Jacquement, S. Beauvière, A. Mbarek, E. Önen, M. Aufort, E. Khaba, C. Girard
Abstract: Click-chemistry… or how to reach (almost) the final fronteer… The use of fast and efficient reactions to access molecular diversity in a blink of an eye… It also gives the oppportunity to play with molecular sub-units to create molecular architecture with infinite creativity. Chemist in all fields are now using this concept and the reactions that have been identified as "clickable". In molecular and medicinal chemistry the use of click-reactions, such as the copper (I)-catalyzed Huisgen's cycloaddition, can give access to a wide range of triazole incorporating molecules. In this field, the preparation of series of molecules is nowadays done by automated approaches (chemical synthesizers, "robots", mini and microreactors in continous flow, etc.). This full paper is presenting the synthesis of a 96-products sized library using a polymer-based copper catalyst that we developped which can be easily separated from the products by simple filtration. This gave us the opportunity to use this catalyst in an automated chemical synthesis station (Chemspeed ASW-2000). Studies and results about the preparation of the catalyst, its use in different solvent systems, its recycling capabilities and it's scope and limitations in the synthesis of this library will be adressed. The synthesis of the triazole library and the very good results obtained will finally be discussed.
Manuscript ID: molecules-clickchem-20090618-Wang-us
Title: Click Reactions Involving the Boronic Acid Moiety: Applications and Potential Issues
Authors: Chaofeng Dai, Yunfeng (Jerry) Cheng, and Binghe Wang *
Affiliation: Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, Georgia, USA 30303; Phone: 404-413-5544, Fax: 404-413-5543, E-mail: wang@gsu.edu
Abstract: Boronic acids have been widely used in a wide range of organic reactions, in the preparation of sensors for carbohydrates, and as potential pharmaceutical agents. The application of copper-mediated Huisgen cycloaddition (click reaction) in the preparation of new boronic acid-containing compounds has allowed for increased structural diversity and synthesis of boronic acids that are otherwise hard to achieve. However, applying this click reaction to the preparation of boronic acids has unique problems. Chief among them is the issue of copper-mediated boronic acid degradation. This review summarizes recent developments, analyses potential issues, and discusses known as well as possible solutions.
Last update: 12 February 2010