Abstract
The last decade has witnessed a tremendous increase of the studies concerning [3+2] cycloaddition reactions of azides and alkynes. The recent discovery of copper(I) species as efficient catalysts for this transformation is at the origin of this true explosion. In contrast with classical thermal reactions, copper catalysis leads to the regioselective formation of 1,4-disubstituted 1,2,3-triazoles in high yields and under simple reaction conditions. This transformation has indeed become the most prominent example of the principles of Click chemistry, postulated in 2001 by Sharpless and co-workers.
Despite the ever-increasing interest in this process, the use of ligands in this context remains minor when compared to ligandless systems. Nevertheless, besides overcoming the inherent limitations of ligandless systems, the use of ligands in this context has been shown to increase and, more importantly, modulate the catalytic activity of the metal center. Herein, the catalytic activities of ligated copper systems are reviewed in a way intended inspirational for future developments in this field.
Keywords: Alkyne, azide, click, copper, cycloaddition, ligand, cycloaddition reactions, regioselective formation, carbon, –, heteroatom bond, stereospecifity, coppercatalyzed azide-alkyne cycloaddion (CuAAC), Amine Ligands, Nitrogen-Based Ligands, N(sp2)-Type Ligands, PHOSPHORUS-BASED LIGANDS
Current Organic Chemistry
Title: The Use of Ligands in Copper-Catalyzed [3+2] Azide-Alkyne Cycloaddition: Clicker than Click Chemistry?
Volume: 15 Issue: 16
Author(s): Silvia Diez-Gonzalez
Affiliation:
Keywords: Alkyne, azide, click, copper, cycloaddition, ligand, cycloaddition reactions, regioselective formation, carbon, –, heteroatom bond, stereospecifity, coppercatalyzed azide-alkyne cycloaddion (CuAAC), Amine Ligands, Nitrogen-Based Ligands, N(sp2)-Type Ligands, PHOSPHORUS-BASED LIGANDS
Abstract: The last decade has witnessed a tremendous increase of the studies concerning [3+2] cycloaddition reactions of azides and alkynes. The recent discovery of copper(I) species as efficient catalysts for this transformation is at the origin of this true explosion. In contrast with classical thermal reactions, copper catalysis leads to the regioselective formation of 1,4-disubstituted 1,2,3-triazoles in high yields and under simple reaction conditions. This transformation has indeed become the most prominent example of the principles of Click chemistry, postulated in 2001 by Sharpless and co-workers.
Despite the ever-increasing interest in this process, the use of ligands in this context remains minor when compared to ligandless systems. Nevertheless, besides overcoming the inherent limitations of ligandless systems, the use of ligands in this context has been shown to increase and, more importantly, modulate the catalytic activity of the metal center. Herein, the catalytic activities of ligated copper systems are reviewed in a way intended inspirational for future developments in this field.
Export Options
About this article
Cite this article as:
Diez-Gonzalez Silvia, The Use of Ligands in Copper-Catalyzed [3+2] Azide-Alkyne Cycloaddition: Clicker than Click Chemistry?, Current Organic Chemistry 2011; 15 (16) . https://dx.doi.org/10.2174/138527211796378488
DOI https://dx.doi.org/10.2174/138527211796378488 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Nanomedicine: Potential Devices for Diagnostics
Recent Patents on Nanomedicine Methods for Biomarker Verification and Assay Development
Current Proteomics New Paradigms in Cellular Function and the Need for Top-Down Proteomics Analysis
Current Proteomics Advances in Parallel Screening of Drug Candidates
Current Medicinal Chemistry Synthesis of New Bis-Spiropyrazoles as Antitumor Agents under Ultrasound Irradiation
Mini-Reviews in Medicinal Chemistry Targeting IAPs as An Approach to Anti-Cancer Therapy
Current Topics in Medicinal Chemistry Recent Progress in Quantitative Proteomics Using Stable Isotope Labeling, Multidimensional Liquid Chromatography and Mass Spectrometry
Current Proteomics Hypoglycaemia and Cardiovascular Disease Risk in Patients with Diabetes
Current Pharmaceutical Design Recent Developments in the Synthesis and Applications of C5-Substituted Pyrimidine Nucleosides and Nucleotides
Current Organic Chemistry Aptamers: Selection, Modification and Application to Nervous System Diseases
Current Medicinal Chemistry Cellular Therapy for Treatment of Stress Urinary Incontinence
Current Stem Cell Research & Therapy 3-(Adamantan-1-yl)-4-hydroxybenzyl Substituted Purines and Pyrimidines: Synthesis and Cytotoxic Activity
Letters in Drug Design & Discovery Combinatorial Dansyl Library and its Applications to pH-Responsive Probes
Combinatorial Chemistry & High Throughput Screening Uncovering New Pharmacological Targets to Treat Neuropathic Pain by Understanding How the Organism Reacts to Nerve Injury
Current Pharmaceutical Design QSAR Multi-Target in Drug Discovery: A Review
Current Computer-Aided Drug Design Effect of Selenium Enrichment of <i>Lenzites betulinus</i> and <i>Trametes hirsuta</i> Mycelia on Antioxidant, Antifungal and Cytostatics Potential
Current Pharmaceutical Biotechnology Sonochemical Hot-spot Assisted One-pot Synthesis of 4-arylmethylidene - 2-phenyl-4H-oxazol-5-ones Using Nano-MgO as an Efficient Catalyst
Letters in Organic Chemistry Applications of Polymeric Nanocapsules in Field of Drug Delivery Systems
Current Drug Discovery Technologies Antibacterial Agents Against Methicillin-Resistant Staphylococcus aureus (MRSA) and Vancomycin-Resistant Enterococci (VRE)
Anti-Infective Agents in Medicinal Chemistry Extraction, Structure and Bioactivities of the Polysaccharides from Fructus corni
Recent Patents on Food, Nutrition & Agriculture