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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.

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Recent Articles

Carbon Nitride Grafted Cobalt Complex (Co@npg-C3N4) for Visible Light−Assisted Esterification of Aldehydes

Carbon Nitride Grafted Cobalt Complex (Co@npg‐C3N4) for Visible Light−Assisted Esterification of Aldehydes

Click reaction was used as an immobilization strategy for heterogenization of cobalt complex to nanoporous graphitic carbon nitride. The synthesized photocatalyst was used for direct esterification reaction of aldehydes with alcohols under visible light irradiation at room temperature. Photocatalyst exhibited higher stability and recyclability for several runs with consistent activity.

[Full Paper]
Anurag Kumar, Pawan Kumar, Abhishek Kumar Pathak, Appala Naidu Chokkapu, Suman L. Jain
ChemistrySelect, April 27, 2017, https://doi.org/10.1002/slct.201602031 Read article

Unclicking the Click: Metal-Assisted Mechanochemical Cycloreversion of Triazoles is Possible

Unclicking the Click: Metal‐Assisted Mechanochemical Cycloreversion of Triazoles is Possible

Mechanochemical unclicking reactions of 1,2,3-triazoles have been a topic of controversy. Based on isotensional quantum-chemical calculations, it is shown that their 1,5-regioisomers easily undergo cycloreversion reactions under standard sonication conditions if they are RuII catalyzed.

[Communication]
Martin Krupička, Przemyslaw Dopieralski, Dominik Marx
Angew. Chem. Int. Ed., April 24, 2017, https://doi.org/10.1002/anie.201612507 Read article

Dendrite Suppression by Synergistic Combination of Solid Polymer Electrolyte Crosslinked with Natural Terpenes and Lithium-Powder Anode for Lithium-Metal Batteries

Dendrite Suppression by Synergistic Combination of Solid Polymer Electrolyte Crosslinked with Natural Terpenes and Lithium‐Powder Anode for Lithium‐Metal Batteries

Let's beat the dendrites! All-solid-state lithium-powder battery comprising solid polymer electrolytes based on natural terpenes and lithium-powder anode is found to be effective for suppressing lithium dendrites. This system can substitute the components of conventional lithium-metal battery such as liquid electrolyte/separator and lithium-foil anode, resulting in realization of safe lithium-metal battery system.

[Full Paper]
Jimin Shim, Jae Won Lee, Ki Yoon Bae, Hee Joong Kim, Woo Young Yoon, Jong-Chan Lee
ChemSusChem, April 21, 2017, https://doi.org/10.1002/cssc.201700408 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

Surface-Triggered Tandem Coupling Reactions of Cyclic Azasilanes

Surface‐Triggered Tandem Coupling Reactions of Cyclic Azasilanes

Working in tandem: Cyclic azasilanes contain a cryptic amine functionality that can perform a subsequent tandem coupling reaction with functional molecules after a surface-triggered ring-opening reaction (see figure), allowing for a one-pot self-assembly route on nanostructures.

[Communication]
Youlin Pan, Annalese Maddox, Taewoo Min, Ferdinand Gonzaga, Jonathan Goff, Barry Arkles
Chem. Asian J., April 06, 2017, https://doi.org/10.1002/asia.201700137 Read article

Synthesis of Syndiotactic Macrocyclic Poly(methyl methacrylate) via Transformation of the Growing Terminal in Stereospecific Anionic Polymerization

Synthesis of Syndiotactic Macrocyclic Poly(methyl methacrylate) via Transformation of the Growing Terminal in Stereospecific Anionic Polymerization

Cyclic syndiotactic poly(methyl methacrylate) (st-PMMA) is synthesized by stereospecific anionic polymerization and intramolecular cyclization. The anionic polymerization is initiated by an α-haloester bearing a protected alkyne via in situ metal-halogen exchange reaction with 1,1-diphenylhexyl lithium and terminated by halogenation of the growing enolate with CBrCl3. After azidation and deprotection, the copper-catalyzed click reaction under high dilution results in the cyclic st-PMMA.

[Full Paper]
Naoya Usuki, Kotaro Satoh, Masami Kamigaito
Macromol. Chem. Phys., March 29, 2017, https://doi.org/10.1002/macp.201700041 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

Synthesis and Self-Assembly of Amphiphilic Block Copolymers from Biobased Hydroxypropyl Methyl Cellulose and Poly(L-lactide)

Synthesis and Self‐Assembly of Amphiphilic Block Copolymers from Biobased Hydroxypropyl Methyl Cellulose and Poly(L‐lactide)

Hydroxypropyl methyl cellulose-block-poly( l-lactide) (HPMC-b-PLLA) diblock copolymers are synthesized via UV-initiated thiol-ene click reaction of thiol-terminated HPMC and allyl-terminated PLLA. The amphiphilic copolymers are able to self-assemble in water, yielding micelles of 50–100 nm. The copolymers exhibit a thermoresponsive behavior with a lower critical solution temperature around 80 °C.

[Full Paper]
Jielin Wang, Marleny Caceres, Suming Li, André Deratani
Macromol. Chem. Phys., March 17, 2017, https://doi.org/10.1002/macp.201600558 Read article

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