The Click Reaction as an Efficient Tool for the Construction of Macrocyclic Structures

Abstract

Abstract:The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC, known as the click reaction) is an established tool used for the construction of complex molecular architectures. Given its efficiency it has been widely applied for bioconjugation, polymer and dendrimer synthesis. More recently, this reaction has been utilized for the efficient formation of rigid or shape-persistent, preorganized macrocyclic species. This strategy also allows the installment of useful functionalities, in the form of polar and function-rich 1,2,3-triazole moieties, directly embedded in the macrocyclic structures. This review analyzes the state of the art in this context, and provides some elements of perspective for future applications.

Polystyrene-supported ionic liquid copper complex: A reusable catalyst for one-pot three-component click reaction

“…Click chemistry, first introduced by the groups of Meldal [6] and Sharpless [7], describes a new concept for conducting organic reactions. Based upon the premise, organic synthesis should take advantages such as being modular, stereospecific, high-yielding and involving simple and green protocols [8]. Preparation of 1,2,3-triazoles by copper-catalysed alkyne-azide cycloaddition (CuAAC) has emerged as a prominent "Click" chemistry [9][10][11].…”

Poly(amide-triazole)s obtained by regioselective, microwave-assisted click polymerization of bio-based monomers

“…to highly defined polymeric materials with unique functional properties such as luminescence, chromism, chain helicity, light refractivity, photovoltaic effect, cytocompatibility and biodegradability [9,10].…”

“…The reaction has been successfully applied in the bio-imaging field, for the labeling of cell surfaces, imaging small molecules inside of living cells or modifying cells with nanomaterials [6]. The CuAAC click reaction is also an established tool for the construction of complex molecular architectures, including polymers [7] and dendrimers [8] and, more recently, for the formation of shape persistent or rigid, preorganized macrocyclic species [9]. Particularly, the click polymerization is a versatile procedure for the synthesis of poly(triazole)s with linear or hyperbranched structures [10].…”

Synthesis of Novel Labdanoid-Based Macroheterocycles Using Click-Cycloaddition Reaction Protocol

“…[12,13] In recent years the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), the most frequently used "click" reaction, have emerged as efficient methodologies for the construction of a range of different macrocyclic structures for different purposes. [14][15][16] CuAAC has been utilized as an efficient protocol to close macrocycles of different sizes by the formation of 1,4-triazoles. [14][15][16][17] During our previous investigation we demonstrated the possibility for construction of macrocyclic compounds on the furan ring of lambertianic acid derivatives.…”

“…[14][15][16] CuAAC has been utilized as an efficient protocol to close macrocycles of different sizes by the formation of 1,4-triazoles. [14][15][16][17] During our previous investigation we demonstrated the possibility for construction of macrocyclic compounds on the furan ring of lambertianic acid derivatives. Furanolabdanoid with 1,2,3-triazole-incorporated macrocycles at C-16 position [18] and furan bridged macrocyclic compounds [19] were obtained and characterized.…”