Hot TopicsWiley-VCH

EJOCADSCChem Eur JAngewandte

Click Chemistry

The term "click chemistry" was introduced by K. Barry Sharpless et al. and denotes the development of a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links. Their Review in Angewandte Chemie in 2001 still ranks among the most accessed online articles in the journal.

Find all articles on click chemistry in Wiley Online Library...

RSS feed

Recent Articles

In-Situ Generated and Premade 1-Copper(I) Alkynes in Cycloadditions

In‐Situ Generated and Premade 1‐Copper(I) Alkynes in Cycloadditions

Based on the investigation of the references and our works on CuAAC reaction, we found the difference and conversion between the in-situ generated and the premade 1-copper(I) alkynes. Finally, the novel carboxylic acid-promoted CuAAC strategy was developed, which has been proven to be the most convenient and highly efficient CuAAC method to date. Furthermore, the novel function of the premade 1-copper(I) alkynes as excellent dipolarophiles was first disclosed and applied. In this article, a series of works reported by our group for the in-situ generated and the premade 1-copper(I) alkynes in cycloadditions are reviewed.

[Personal Account]
Xinyan Wang, Xingyong Wang, Xuesong Wang, Jianlan Zhang, Chulong Liu, Yuefei Hu
Chem. Rec., June 22, 2017, https://doi.org/10.1002/tcr.201700011 Read article

Click Glycosylation for the Synthesis of 1,2,3-Triazole-Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity

Click Glycosylation for the Synthesis of 1,2,3‐Triazole‐Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity

A group of 1,2,3-triazole-linked picropodophyllotoxin glycoconjugates were synthesized through Cu(I)-catalyzed click glycosylation reactions. Azido-functionalized podophyllotoxin derivatives were coupled with various oligosaccharide building blocks, followed by treatment with NaOCH3 to facilitate global deacylation and epimerization at C-2 position, affording the target picropodophyllotoxin glycoconjugates in good yield. In vitro MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay shows that compound 27 exhibits potent anticancer activity against all five cancer cell lines tested.

[Full Paper]
Cheng-Ting Zi, Liu Yang, Wei Gao, Yan Li, Jun Zhou, Zhong-Tao Ding, Jiang-Miao Hu, Zi-Hua Jiang
ChemistrySelect, June 22, 2017, https://doi.org/10.1002/slct.201700347 Read article

Synthesis of BODIPY-Labeled Cholesterylated Glycopeptides by Tandem Click Chemistry for Glycocalyxification of Giant Unilamellar Vesicles (GUVs)

Synthesis of BODIPY‐Labeled Cholesterylated Glycopeptides by Tandem Click Chemistry for Glycocalyxification of Giant Unilamellar Vesicles (GUVs)

Double functionalization of cholesterylated peptide constructs by site-specific tandem click chemistry is described. Copper-free click attachment of a bicyclononyne fluorophore succeeded by copper(I)-catalyzed clicking on an azido-glycan.

[Communication]
Nicolai Stuhr-Hansen, Charikleia-Despoina Vagianou, Ola Blixt
Chem. Eur. J., June 22, 2017, https://doi.org/10.1002/chem.201702104 Read article

Photocontrollable Supramolecular Self-Assembly of a Porphyrin Derivative that Contains a Polyhedral Oligomeric Silsesquioxane (POSS)

Photocontrollable Supramolecular Self‐Assembly of a Porphyrin Derivative that Contains a Polyhedral Oligomeric Silsesquioxane (POSS)

Hugo POSS: A photosensitive organic–inorganic hybrid porphyrin (H2TPP−Azo−POSS) exhibited a tunable morphology by simply changing the concentration and polarity of the solvent. Spherical micelles and linear nanowires were formed in CHCl3, whilst vesicles were formed in CHCl3/n-hexane. The morphologies of H2TPP−Azo−POSS demonstrated a light-triggered transition, whilst the size of the aggregates decreased under UV irradiation.

[Full Paper]
Yong Zhang, Tao Yue, Hongliang Cao, Yun Gao, Weian Zhang
Asian J. Org. Chem., June 09, 2017, https://doi.org/10.1002/ajoc.201700223 Read article

Efficient Polymer-Polymer Conjugation via Thiol-ene Click Reaction

Efficient Polymer‐Polymer Conjugation via Thiol‐ene Click Reaction

Considerations particular to radical thiol-ene conjugation of polymers are reviewed. Mitigation of characteristic challenges is discussed and the successful coupling of polymers via radical thiol-ene reaction is demonstrated. Both functional group and initiator determine the extent of successful polymer-polmyer coupling.

[Trend]
Benjamin D. Fairbanks, Dillon M. Love, Christopher N. Bowman
Macromol. Chem. Phys., June 08, 2017, https://doi.org/10.1002/macp.201700073 Read article

1,2,4-Triazine-Modified 2′-Deoxyuridine Triphosphate for Efficient Bioorthogonal Fluorescent Labeling of DNA

1,2,4‐Triazine‐Modified 2′‐Deoxyuridine Triphosphate for Efficient Bioorthogonal Fluorescent Labeling of DNA

A better way to click: 1,2,4-Triazene-modified nucleotide triphosphates were synthesized and shown to be accepted as substrates by DNA polymerases. This new bioorthogonal modification could be an improvement over the problematic 1,2,4,5-tetrazines for postsynthetic fluorescent labeling of DNA by Diels–Alder reactions with inverse electron demand.

[Communication]
Krisana Peewasan, Hans-Achim Wagenknecht
ChemBioChem, June 07, 2017, https://doi.org/10.1002/cbic.201700185 Read article

Click-Chemistry-Mediated Rapid Microbubble Capture for Acute Thrombus Ultrasound Molecular Imaging

Click‐Chemistry‐Mediated Rapid Microbubble Capture for Acute Thrombus Ultrasound Molecular Imaging

Real-time thrombosis imaging: Click coupling between tetrazine-modified microbubbles and CD62p tagged with trans-cyclooctene allows a fast, reliable, and highly sensitive ultrasound molecular imaging approach to capture activated-platelet-specific CD62p-targeted thrombus. This method could be a simple but powerful tool for rapid and real-time diagnosis of acute thrombosis.

[Communication]
Tuantuan Wang, Chuxiao Yuan, Bingyang Dai, Yang Liu, Mingxi Li, Zhenqiang Feng, Qing Jiang, Zhihong Xu, Ningwei Zhao, Ning Gu, Fang Yang
ChemBioChem, June 07, 2017, https://doi.org/10.1002/cbic.201700068 Read article

Efficient Homodifunctional Bimolecular Ring-Closure Method for Cyclic Polymers by Combining RAFT and Self-Accelerating Click Reaction

Efficient Homodifunctional Bimolecular Ring‐Closure Method for Cyclic Polymers by Combining RAFT and Self‐Accelerating Click Reaction

A metal-free homodifunctional bimolecular ring-closure method is developed for preparing cyclic polymers by combining reversible addition-fragmentation chain transfer polymerization and self-accelerating double strain-promoted azide–alkyne click (DSPAAC) reaction. The self-accelerating property of DSPAAC ring-closing reaction facilitates this novel method to efficiently produce pure cyclic polymers by virtue of an excess molar amount of smaller linkers to ring-close the corresponding linear polymer precursors.

[Communication]
Lin Qu, Peng Sun, Ying Wu, Ke Zhang, Zhengping Liu
Macromol. Rapid Commun., May 31, 2017, https://doi.org/10.1002/marc.201700121 Read article

Expanding the Scope of Metabolic Glycan Labeling in Arabidopsis thaliana

Expanding the Scope of Metabolic Glycan Labeling in Arabidopsis thaliana

Metabolic glycan labeling (MGL) in plants: A collection of 19 unnatural sugars containing a bioorthogonal group (that is, an azide, alkyne, or cyclopropene) were synthesized, and their performance in of MGL was evaluated by fluorescence imaging of root glycans in Arabidopsis thaliana.

[Full Paper]
Yuntao Zhu, Xing Chen
ChemBioChem, May 23, 2017, https://doi.org/10.1002/cbic.201700069 Read article

Chemoenzymatic Synthesis of Triazololactams Structurally Related to Pancratistatin

Chemoenzymatic Synthesis of Triazololactams Structurally Related to Pancratistatin

The synthesis of previously unknown tricyclic lactams that resemble the basic skeleton of the phenanthridone Amaryllidaceae alkaloid family is achieved with high optical purity in 13 steps from bromobenzene. The strategy combines a chemoenzymatic procedure to construct the cyclitol moiety with an uncatalyzed version of the Huisgen reaction and a solvent-free cyclization to build the lactam ring.

[Communication]
Victoria de la Sovera, Leopoldo Suescun, Ana Bellomo, David Gonzalez
Eur. J. Org. Chem., May 15, 2017, https://doi.org/10.1002/ejoc.201700334 Read article

Covalent Incorporation of Ionic Liquid into Ion-Conductive Networks via Thiol–Ene Photopolymerization

Covalent Incorporation of Ionic Liquid into Ion‐Conductive Networks via Thiol–Ene Photopolymerization

Photoinitiated polymerization and crosslinking of ionic liquid monomers with thiol and ene comonomers provides rapid, tunable, and spatially controlled formation of thiol–ene networks with higher ionic conductivity, glass transition temperature, and heterogeneity than their noncharged analogs. The interaction strength between cation and anion largely dictates the resultant thiol–ene poly(ionic liquid) network properties.

[Communication]
Andrew C. Tibbits, Yushan S. Yan, Christopher J. Kloxin
Macromol. Rapid Commun., May 04, 2017, https://doi.org/10.1002/marc.201700113 Read article

Electronic Influences on the Stability and Kinetics of Cp* Rhodium(III) Azide Complexes in the iClick Reaction with Electron-Poor Alkynes

Electronic Influences on the Stability and Kinetics of Cp* Rhodium(III) Azide Complexes in the iClick Reaction with Electron‐Poor Alkynes

RhIII azide complexes of general formula [Rh(Cp*)(N3)(bpyR,R)]+ with electron-withdrawing or -donating substituents R react in a catalyst-free, room-temperature click reaction with electron-poor alkynes to form stable triazolates. Pseudo-first-order rate constants determined with solution IR spectroscopy are comparable to those of the Staudinger ligation used for bio(macro)molecule functionalization.

[Full Paper]
Luisa Waag-Hiersch, Jan Mößeler, Ulrich Schatzschneider
Eur. J. Inorg. Chem., April 20, 2017, https://doi.org/10.1002/ejic.201700199 Read article

Controllable Superhydrophobic Coating on Cotton Fabric by UV Induced Thiol-ene Reaction for Wettability Patterning and Device Metallization

Controllable Superhydrophobic Coating on Cotton Fabric by UV Induced Thiol‐ene Reaction for Wettability Patterning and Device Metallization

A special controllable superhydrophobic surface is constructed on cotton fabric. After thiol treatment and UV irradiation, the surface quickly changes to superhydrophilic state. The fast wettabiltiy switch can be applied for surface patterning and device metallization.

[Full Paper]
Shu Deng, Jianying Huang, Zhong Chen, Yuekun Lai
Adv. Mater. Interfaces, April 20, 2017, https://doi.org/10.1002/admi.201700268 Read article

A Scalable and Versatile Synthesis of Oxime-Based Hormone Dimers and Gels for Sustained Release

A Scalable and Versatile Synthesis of Oxime‐Based Hormone Dimers and Gels for Sustained Release

Keeping hormones in balance: Well-defined steroid hormone dimers and organogels were produced via a facile and scalable synthesis using oxime click chemistry. Owing to the dynamic oxime bonds, the hormone-based materials are degradable via acidic hydrolysis and transoximination, therefore representing new materials for the controlled release of steroid hormones.

[Communication]
Christopher W. Bennett, Joe Collins, Zeyun Xiao, Daniel Klinger, Luke A. Connal
Chem. Asian J., April 18, 2017, https://doi.org/10.1002/asia.201700288 Read article

Electrode Modification Through Click Chemistry using Ni and Co Alkyne Phthalocyanines for Electrocatalytic Detection of Hydrazine

Electrode Modification Through Click Chemistry using Ni and Co Alkyne Phthalocyanines for Electrocatalytic Detection of Hydrazine

[Full Paper]
Charles S. J. N. O'Donoghue, Munyaradzi Shumba, Tebello Nyokong
Electroanalysis, April 12, 2017, https://doi.org/10.1002/elan.201700084 Read article

Azido Pentoses: A New Tool To Efficiently Label Mycobacterium tuberculosis Clinical Isolates

Azido Pentoses: A New Tool To Efficiently Label Mycobacterium tuberculosis Clinical Isolates

Sugar for tuberculosis: Azido pentoses show excellent labeling of Mycobacterium tuberculosis without affecting pathogenicity in macrophages, by exploiting the unique structure of the Mycobacterium cell wall. The three developed azido pentoses could serve as robust tools for virulence studies with Mycobacterium clinical isolates.

[Communication]
Katharina Kolbe, Leonhard Möckl, Victoria Sohst, Julius Brandenburg, Regina Engel, Sven Malm, Christoph Bräuchle, Otto Holst, Thisbe K. Lindhorst, Norbert Reiling
ChemBioChem, March 29, 2017, https://doi.org/10.1002/cbic.201600706 Read article

© Wiley-VCH 2016.