Thiol–yne coupling: revisiting old concepts as a breakthrough for up-to-date applications

Macromol. Biosci. 11/2011

(2012) Miguel Lomba et al.   MACROMOLECULAR BIOSCIENCE

A “Tag-and-Modify” Approach to Site-Selective Protein Modification

(2011) Justin M. Chalker et al.   ACCOUNTS OF CHEMICAL RESEARCH

Thiol-yne Reaction on Boron-Doped Diamond Electrodes: Application for the Electrochemical Detection of DNA–DNA Hybridization Events

(2011) Dalila Meziane et al.   ANALYTICAL CHEMISTRY

Multifunctional Trackable Dendritic Scaffolds and Delivery Agents

(2011) Roey J. Amir et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Reliable and Efficient Procedures for the Conjugation of Biomolecules through Huisgen Azide-Alkyne Cycloadditions

(2011) Enrique Lallana et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Regenerative Biomaterials that “Click”: Simple, Aqueous-Based Protocols for Hydrogel Synthesis, Surface Immobilization, and 3D Patterning

(2011) Chelsea M. Nimmo et al.   BIOCONJUGATE CHEMISTRY

Thiol–yne and Thiol–ene “Click” Chemistry as a Tool for a Variety of Platinum Drug Delivery Carriers, from Statistical Copolymers to Crosslinked Micelles

(2011) Vien T. Huynh et al.   BIOMACROMOLECULES

Heterogeneous Hydrothiolation of Alkynes with Thiols Catalyzed by Diphosphino-Functionalized MCM-41 Anchored Rhodium Complex

(2011) Hong Zhao et al.   CATALYSIS LETTERS

Revealing the nature of thio-click reactions on the solid phase

(2011) M. Talha Gokmen et al.   CHEMICAL COMMUNICATIONS

Surface glycosylation of polymer membrane by thiol-yne click chemistry for affinity adsorption of lectin

(2011) Cang Wang et al.   CHEMICAL COMMUNICATIONS

Facile functionalization of polypeptides by thiol-yne photochemistry for biomimetic materials synthesis

(2011) Yugang Huang et al.   CHEMICAL COMMUNICATIONS

Multi-molecule reaction of serum albumin can occur through thiol-yne coupling

(2011) Mauro Lo Conte et al.   CHEMICAL COMMUNICATIONS

Recent applications of thiol–ene coupling as a click process for glycoconjugation

(2011) Alessandro Dondoni et al.   CHEMICAL SOCIETY REVIEWS

Reactions under the Click Chemistry Philosophy Employed in Supramolecular and Mechanostereochemical Systems

(2011) Albert C. Fahrenbach et al.   Chemistry-An Asian Journal

Synthesis of multifunctional polymer brush surfaces via sequential and orthogonal thiol-click reactions

(2011) Santosh B. Rahane et al.   JOURNAL OF MATERIALS CHEMISTRY

Thiol-alkyne Chemistry for the Preparation of Micelles with Glycopolymer Corona: Dendritic Surfaces versus Linear Glycopolymer in Their Ability to Bind to Lectins

(2011) Jatin Kumar et al.   MACROMOLECULAR RAPID COMMUNICATIONS

Poly(vinylidene fluoride) Graft Copolymer Membranes with “Clickable” Surfaces and Their Functionalization

(2011) Tao Cai et al.   MACROMOLECULES

Spatial and temporal control of the alkyne–azide cycloaddition by photoinitiated Cu(II) reduction

(2011) Brian J. Adzima et al.   Nature Chemistry

Click chemistry by microcontact printing on self-assembled monolayers: A structure–reactivity study by fluorescence microscopy

(2011) Jan Mehlich et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Luminescent Hyperbranched Polymers: Combining Thiol-Yne Chemistry with Gold-Mediated C−H Bond Activation

(2011) Dominik Konkolewicz et al.   ORGANOMETALLICS

Sequential click synthesis of hyperbranched polymers via the A2 + CB2 approach

(2011) Jin Han et al.   Polymer Chemistry

Thiol-Yne Chemistry: A Powerful Tool for Creating Highly Functional Materials

(2010) Richard Hoogenboom   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Thiol-Ene Click Chemistry

(2010) Charles E. Hoyle et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Thiol-Based 'Click' Chemistries in Polymer: Synthesis and Modification

(2010) Andrew B. Lowe et al.   AUSTRALIAN JOURNAL OF CHEMISTRY

Radical Additions of Arenethiols to Ynamides for the Selective Synthesis of N-[(Z)-2-(Arylsulfanyl)-1-alkenyl]amides

(2010) Akinori Sato et al.   BULLETIN OF THE KOREAN CHEMICAL SOCIETY

Synthesis of cyclic, multivalent Arg-Gly-Asp using sequential thiol–ene/thiol–yne photoreactions

(2010) Alex A. Aimetti et al.   CHEMICAL COMMUNICATIONS

“Click” methodologies: efficient, simple and greener routes to design dendrimers

(2010) Grégory Franc et al.   CHEMICAL SOCIETY REVIEWS

Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis

(2010) Charles E. Hoyle et al.   CHEMICAL SOCIETY REVIEWS

Cu-free click cycloaddition reactions in chemical biology

(2010) John C. Jewett et al.   CHEMICAL SOCIETY REVIEWS

Synthesis of glycopolymers via click reactions

(2010) Stacy Slavin et al.   EUROPEAN POLYMER JOURNAL

Thiol-yne click chemistry: A powerful and versatile methodology for materials synthesis

(2010) Andrew B. Lowe et al.   JOURNAL OF MATERIALS CHEMISTRY

Photoinduced Addition of Glycosyl Thiols to Alkynyl Peptides: Use of Free-Radical Thiol−Yne Coupling for Post-Translational Double-Glycosylation of Peptides

(2010) Mauro Lo Conte et al.   JOURNAL OF ORGANIC CHEMISTRY

An Insight into the Radical Thiol/Yne Coupling: The Emergence of Arylalkyne-Tagged Sugars for the Direct Photoinduced Glycosylation of Cysteine-Containing Peptides

(2010) Matteo Minozzi et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthetic evolutions in the nucleophilic addition to alkynes

(2010) Bo Xu et al.   JOURNAL OF ORGANOMETALLIC CHEMISTRY

The power of thiol-ene chemistry

(2010) Matthew J. Kade et al.   JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY

Organozirconium Complexes as Catalysts for Markovnikov-Selective Intermolecular Hydrothiolation of Terminal Alkynes: Scope and Mechanism

(2010) Charles J. Weiss et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Carbohydrate Microarrays by Microcontact Printing

(2010) Christian Wendeln et al.   LANGMUIR

High-Density Glycosylation of Polymer Membrane Surfaces by Click Chemistry for Carbohydrate-Protein Recognition

(2010) Cang Wang et al.   MACROMOLECULAR RAPID COMMUNICATIONS

Synthesis, Thiol−Yne “Click” Photopolymerization, and Physical Properties of Networks Derived from Novel Multifunctional Alkynes

(2010) Justin W. Chan et al.   MACROMOLECULES

Stress Relaxation by Addition−Fragmentation Chain Transfer in Highly Cross-Linked Thiol−Yne Networks

(2010) Hee Young Park et al.   MACROMOLECULES

Versatile Strategy for the Synthesis of Hyperbranched Poly(ε-caprolactone)s and Polypseudorotaxanes Thereof

(2010) Wei Liu et al.   MACROMOLECULES

Reaction Rates and Mechanisms for Radical, Photoinitated Addition of Thiols to Alkynes, and Implications for Thiol−Yne Photopolymerizations and Click Reactions

(2010) Benjamin D. Fairbanks et al.   MACROMOLECULES

Highly Branched and Hyperbranched Glycopolymers via Reversible Addition−Fragmentation Chain Transfer Polymerization and Click Chemistry

(2010) Mona Semsarilar et al.   MACROMOLECULES

Thiol−Yne Click Polymerization: Regio- and Stereoselective Synthesis of Sulfur-Rich Acetylenic Polymers with Controllable Chain Conformations and Tunable Optical Properties

(2010) Jianzhao Liu et al.   MACROMOLECULES

Synthesis of Sulfuric Macrocycles and a Rotaxane through Thiol-yne Click and Dithiol Coupling Reactions

(2010) Weidong Zhou et al.   ORGANIC LETTERS

Thiol-ene and thiol-yne chemistry in microfluidics: a straightforward method towards macroporous and nonporous functional polymer beads

(2010) R. Arun Prasath et al.   Polymer Chemistry

Thiol–yne ‘click’ chemistry as a route to functional lipid mimetics

(2010) Sandeep S. Naik et al.   Polymer Chemistry

Fast and Sensitive Pretargeted Labeling of Cancer Cells through a Tetrazine/trans-Cyclooctene Cycloaddition

(2009) Neal K. Devaraj et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Fast Alkene Functionalization In Vivo by Photoclick Chemistry: HOMO Lifting of Nitrile Imine Dipoles

(2009) Yizhong Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Bioorthogonal Ligation in the Spotlight

(2009) Thomas Kurpiers et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Click Chemistry beyond Metal-Catalyzed Cycloaddition

(2009) C. Remzi Becer et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality

(2009) Ellen M. Sletten et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Efficient synthesis of vinyl and alkyl sulfides via hydrothiolation of alkynes and electron-deficient olefins using soluble and heterogenized gold complexes catalysts

(2009) Avelino Corma et al.   APPLIED CATALYSIS A-GENERAL

Synthesis and Applications of Biomedical and Pharmaceutical Polymers via Click Chemistry Methodologies

(2009) Maarten van Dijk et al.   BIOCONJUGATE CHEMISTRY

Water-promoted regioselective hydrothiolation of alkynes

(2009) Sukalyan Bhadra et al.   CANADIAN JOURNAL OF CHEMISTRY

Enabling olefin metathesis on proteins: chemical methods for installation of S-allyl cysteine

(2009) Justin M. Chalker et al.   CHEMICAL COMMUNICATIONS

Efficient synthesis of dendrimers via a thiol–yne and esterification process and their potential application in the delivery of platinum anti-cancer drugs

(2009) Gaojian Chen et al.   CHEMICAL COMMUNICATIONS

Synthesis of Well-Defined Polypeptide-Based Materials via the Ring-Opening Polymerization of α-Amino AcidN-Carboxyanhydrides

(2009) Nikos Hadjichristidis et al.   CHEMICAL REVIEWS

Photopolymerization of Thiol-Alkynes: Polysulfide Networks

(2009) Justin W. Chan et al.   CHEMISTRY OF MATERIALS

Electron-Deficient Alkynes as Cleavable Reagents for the Modification of Cysteine-Containing Peptides in Aqueous Medium

(2009) Hoi-Yan Shiu et al.   CHEMISTRY-A EUROPEAN JOURNAL

A New Ligation Strategy for Peptide and Protein Glycosylation: Photoinduced Thiol-Ene Coupling

(2009) Alessandro Dondoni et al.   CHEMISTRY-A EUROPEAN JOURNAL

Radical Additions of Thiols to Alkenes and Alkynes in Ionic Liquids

(2009) Tommaso Lanza et al.   CURRENT ORGANIC CHEMISTRY

Rhodium(I) and iridium(I) complexes containing bidentate phosphine-imidazolyl donor ligands as catalysts for the hydroamination and hydrothiolation of alkynes

(2009) Leslie D. Field et al.   DALTON TRANSACTIONS

Microcontact chemistry: surface reactions in nanoscale confinement

(2009) Bart Jan Ravoo   JOURNAL OF MATERIALS CHEMISTRY

Inverse-electron-demand Diels-Alder reaction as a highly efficient chemoselective ligation procedure: Synthesis and function of a BioShuttle for temozolomide transport into prostate cancer cells

(2009) Rüdiger Pipkorn et al.   JOURNAL OF PEPTIDE SCIENCE

Sequential thiol-ene/thiol-ene and thiol-ene/thiol-yne reactions as a route to well-defined mono and bis end-functionalized poly(N-isopropylacrylamide)

(2009) Bing Yu et al.   JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY

Organoactinide-Mediated Hydrothiolation of Terminal Alkynes with Aliphatic, Aromatic, and Benzylic Thiols

(2009) Charles J. Weiss et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Sequential Phosphine-Catalyzed, Nucleophilic Thiol−Ene/Radical-Mediated Thiol−Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials

(2009) Justin W. Chan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

“Clicking” Polymer Brushes with Thiol-yne Chemistry: Indoors and Out

(2009) Ryan M. Hensarling et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Hyperbranched Polymers by Thiol−Yne Chemistry: From Small Molecules to Functional Polymers

(2009) Dominik Konkolewicz et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Macromolecular Engineering through Click Chemistry and Other Efficient Transformations

(2009) Brent S. Sumerlin et al.   MACROMOLECULES

Sequential click reactions for synthesizing and patterning three-dimensional cell microenvironments

(2009) Cole A. DeForest et al.   NATURE MATERIALS

Copper-Free “Click” Modification of DNA via Nitrile Oxide−Norbornene 1,3-Dipolar Cycloaddition

(2009) Katrin Gutsmiedl et al.   ORGANIC LETTERS

Reductive Addition of the Benzenethiyl Radical to Alkynes by Amine-Mediated Single Electron Transfer Reaction to Diphenyl Disulfide

(2009) Tsuyoshi Taniguchi et al.   ORGANIC LETTERS

An easy access to pyrimidine-fused azocine derivatives by thiophenol-mediated radical cyclization via 8-endo-trig mode

(2009) K.C. Majumdar et al.   TETRAHEDRON LETTERS

A Photoinducible 1,3-Dipolar Cycloaddition Reaction for Rapid, Selective Modification of Tetrazole-Containing Proteins

(2008) Wenjiao Song et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

The Emergence of Thiol-Ene Coupling as a Click Process for Materials and Bioorganic Chemistry

(2008) Alessandro Dondoni   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell Imaging

(2008) Neal K. Devaraj et al.   BIOCONJUGATE CHEMISTRY

Copper-free click chemistry for the in situ crosslinking of photodegradable star polymers

(2008) Jeremiah A. Johnson et al.   CHEMICAL COMMUNICATIONS

Glycoprotein Synthesis: An Update

(2008) David P. Gamblin et al.   CHEMICAL REVIEWS

Synthesis of 1,1-Disubstituted Alkyl Vinyl Sulfides via Rhodium-Catalyzed Alkyne Hydrothiolation: Scope and Limitations

(2008) Jun Yang et al.   JOURNAL OF ORGANIC CHEMISTRY

Selective Functionalization of a Genetically Encoded Alkene-Containing Protein via “Photoclick Chemistry” in Bacterial Cells

(2008) Wenjiao Song et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Robust, Efficient, and Orthogonal Synthesis of Dendrimers via Thiol-ene “Click” Chemistry

(2008) Kato L. Killops et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity

(2008) Melissa L. Blackman et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Thiol−Yne Photopolymerizations: Novel Mechanism, Kinetics, and Step-Growth Formation of Highly Cross-Linked Networks

(2008) Benjamin D. Fairbanks et al.   MACROMOLECULES

Tin-Free Generation of Alkyl Radicals from Alkyl 4-Pentynyl Sulfides via Homolytic Substitution at the Sulfur Atom†

(2008) Giorgio Bencivenni et al.   ORGANIC LETTERS

Synthesis of 1,1-Disubstituted Olefins via Catalytic Alkyne Hydrothiolation/Kumada Cross-Coupling

(2008) Anthony Sabarre et al.   ORGANIC LETTERS

In Vivo Imaging of Membrane-Associated Glycans in Developing Zebrafish

(2008) S. T. Laughlin et al.   SCIENCE

Thiol-mediated radical cyclizations

(2008) Krishna C. Majumdar et al.   TETRAHEDRON

Synthesis of vinyl sulfides via hydrothiolation of alkynes using Al2O3/KF under solvent-free conditions

(2008) Márcio S. Silva et al.   TETRAHEDRON LETTERS

Thiophenol-mediated intramolecular radical cyclization: an efficient method for the synthesis of benzoxocine derivatives

(2008) Krishna C. Majumdar et al.   TETRAHEDRON LETTERS

Wittig olefination and thiol mediated 7-endo-trig radical cyclization: novel synthesis of oxepin derivatives

(2008) K.C. Majumdar et al.   TETRAHEDRON LETTERS

Photoexcitation of tryptophan groups induced reduction of disulfide bonds in hen egg white lysozyme

(2007) Ling-Zhi Wu et al.   JOURNAL OF MOLECULAR STRUCTURE