CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• conjugates. In addition to this, the fluorescence studies suggested that the energy transfer was not efficient in Zn(II) porphyrin-BODIPY and 21,23-dithiaporphyrin-BODIPY conjugates. Dalip Kumar and his co-workers reported a CuAAC click reaction to prepare novel water soluble triazole-linked cationic

• zinc porphyrin sensitizer with a H2-evolving cobalt diimine dioxime catalyst. First, the Zn porphyrin 88b was coupled with the copper diiminedioxime complex 89 via the CuAAC click reaction to give porphyrin complex 90 in 74% yield (Scheme 18). Furthermore, a stable Co(III) complex was obtained by the

• groups by using a CuAAC click reaction between azide and acetylene-substituted porphyrins in good yields as shown in Scheme 21. The photophysical and electrochemical studies along with DFT calculations showed that these dyads possess suitable frontier orbital energy levels for the use as sensitizers in

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• silyl groups. Both other reagents used for the cleavage in CD chemistry (TBAF and BF3.Et2O) yielded byproducts that unnecessarily complicated the purification. The CuAAC "click reaction" in CD chemistry is also a well-known approach, allowing coupling reactions of azido-containing CDs with different

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• ) or Ni(II) with N-propargylmaleimide via the CuAAC click reaction to afford fluorinated porphyrin–triazole–maleimide conjugates. New maleimide derivatives were isolated in reasonable yields and identified by UV–vis, 1H NMR, 19F NMR spectroscopy and mass-spectrometry. Keywords: chlorin; maleimide

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• (iodine, bromine) and chalcogens (selenium and tellurium) [18]. While there are several strategies for the synthesis of triazoles, the Cu(II)-catalyzed azide–alkyne cycloaddition reaction (CuAAC click reaction) is considered as one of the most efficient, simple and mild approaches towards the preparation

• template-directed self-assembly procedure via an intramolecular “CuAAC click” reaction in the presence of electron-rich bisnaphtho- or bisbenzo-24-crown-8 ethers. Afterwards, the triazole groups in the catenanes were methylated. The resulting triazolium macrocycle containing catenanes 17a (DN24C8) and 17b

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

• Guojuan Li,
• Chunying Fan,
• Guo Cheng,
• Wanhua Wu and
• Cheng Yang

Beilstein J. Org. Chem. 2019, 15, 1601–1611, doi:10.3762/bjoc.15.164

• assigned to the excimer emission of Py (Figure S23, Supporting Information File 1) [54]. Conclusion Two new planar chiral macrocyclic hosts P5A-DPA and P5A-Py were synthesized by grafting two fluorophore pigments (DPA or Py) on pillar[5]arene through CuAAC “click” reaction. The new macrocyclic compounds

New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

• Iveta Chena Tichá,
• Simona Hybelbauerová and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2019, 15, 830–839, doi:10.3762/bjoc.15.80

• derivatives monosubstituted with cinchona alkaloids (cinchonine, cinchonidine, quinine and quinidine) on the primary rim through a CuAAC click reaction. Subsequently, permethylated analogs of these cinchona alkaloid–CD derivatives also were synthesized and the catalytic activity of all derivatives was

• ; cinchona alkaloids; CuAAC click reaction; cyclodextrin; organocatalysts; Introduction Cyclodextrins (CDs) [1], cyclic oligosaccharides consisting of α-D-glucopyranoside units, and their derivatives are widely used in many industrial and research areas for their ability to form supramolecular inclusion

• required starting materials 6I-azido-6I-deoxy-α-CD (1) [27] and 6I-azido-6I-deoxy-β-CD (2) [27] and 9-O-propargylated cinchona alkaloid derivatives 3a–d [28] were synthesized followed by optimization of the conditions for the CuAAC click reaction (Scheme 1). The CuAAC click reaction conditions were

Nucleoside macrocycles formed by intramolecular click reaction: efficient cyclization of pyrimidine nucleosides decorated with 5'-azido residues and 5-octadiynyl side chains

• Jiang Liu,
• Peter Leonard,
• Sebastian L. Müller,
• Constantin Daniliuc and
• Frank Seela

Beilstein J. Org. Chem. 2018, 14, 2404–2410, doi:10.3762/bjoc.14.217

• intramolecular cyclization to a macrocycle was not observed. Next, the 5’-azido compound 2 was employed in the copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) "click" reaction [38][39] to build up macrocycle 3. In this regard, two reaction pathways have to be considered: (i) an intramolecular “click

An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change

• Tomoki Ogoshi,
• Tomohiro Akutsu and
• Tada-aki Yamagishi

Beilstein J. Org. Chem. 2018, 14, 1937–1943, doi:10.3762/bjoc.14.167

• (CuAAC) ‘‘click’’ reaction (see details in the experimental section). In addition, model compound 4 was also synthesized as a reference (Figure 1d). Compound 3 is soluble in various organic and aqueous solvents as it comprises eight amphiphilic tri(ethylene oxide) chains. We investigated the

An uracil-linked hydroxyflavone probe for the recognition of ATP

• Márton Bojtár,
• Péter Zoltán Janzsó-Berend,
• Dávid Mester,
• Dóra Hessz,
• Mihály Kállay,
• Miklós Kubinyi and
• István Bitter

Beilstein J. Org. Chem. 2018, 14, 747–755, doi:10.3762/bjoc.14.63

• further stabilizes the complex, and this structure is energetically more favorable. These results prompted us towards the synthesis and evaluation of this promising molecule. Synthesis The synthesis of UHF is depicted in Scheme 1. UHF was synthesized by the CuAAC (click) reaction of 7-propargyloxy-3

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• click reaction to provide the target 6-phenyl-2-(trifluoromethyl)quinolines containing p-halogen-substituted and non-substituted phenyl-1,2,3-triazole unit attached at the O-4 position of the quinoline fragment. All triazole products have almost identical conformations in the solid state, with no

• the interactions between the present halogen atoms were not observed. For more detailed description of crystal structures of 5–8 please refer to the section 7 of Supporting Information File 1 and Figures S23–S28 therein. Conclusion In conclusion, mechanochemistry was successfully applied in CuAAC

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• ). Disfavored mononuclear pathway and favored dinuclear pathway in the CuAAC click reaction, according to the mechanistic proposal of reference [37]. R, R’ = alkyl, aryl, silyl, carbonyl groups; L = NHC; L’ = NHC or solvent; L’’ = solvent, acetylide, carboxylate, halide. Synthesis of dinuclear copper complex 2

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• defined a 1,2,3-triazole containing linkage between two piperidine rings as the flexible joint F, which should be easily accessible by copper-catalyzed cycloaddition between an azide G and a terminal alkyne H (CuAAC, “Click” reaction) [16]. Primary alcohols I serve as “protected” azides accessible by

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

• Silvia Bernardi,
• Paola Fezzardi,
• Gabriele Rispoli,
• Stefania E. Sestito,
• Francesco Peri,
• Francesco Sansone and
• Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

• and pyridine 7:3 as previously described for compound 8. The CuAAC “click” reaction was carried out as previously described for the galacto-clusters 9 and 13 and afforded the cone calix[4]arene 16 (Scheme 3) and 1,3-alternate calix[4]arene 19 (Scheme 4) in 46% isolated yield. Microwave irradiation

The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• delivery. Many other fields have utilised the copper-catalysed azide–alkyne cycloaddition (CuAAC) ‘click’ reaction [16][17] to generate libraries of compounds, including enzyme inhibitors [18][19][20], catalysis ligands [21][22][23] and metal frameworks [24][25]. We have recently demonstrated that a

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

• Yoann M. Chabre,
• Alex Papadopoulos,
• Alexandre A. Arnold and
• René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

• shown). Synthesis of mannosylated trimers 5 and 9 using trimesic acid core transformed into propargylated (2) and azidopropylated (6) scaffolds and then coupled by “click chemistry” with either 2-azidoethyl (3) or propargyl (7) mannopyranosides. Divergent CuAAc “click reaction” between propargylated

Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability

• Malamatenia D. Manouilidou,
• Yannis G. Lazarou,
• Irene M. Mavridis and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 774–783, doi:10.3762/bjoc.10.73

• . These include the well-known copper-catalyzed azide–alkyne cyclization (CuAAC, “click” reaction) between an azido-CD derivative and an alkyne linker [19][22][23][24] [22], or vice versa, the metal catalyzed reactions between propargyl-CDs and aryl dihalides such as the Sonogashira and Glaser–Hay