An experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide with sodium azide in DMA under microwave heating. Subsequent addition of [RuClCp*(PPh(3))(2)] and the alkyne yielded...

Unprecedented tetracyclic polymer topologies with spiro- and a bridged-type quatrefoil forms are effectively constructed through an alkyne-azide, click-linking reaction by employing a kyklo-telechelic poly(tetrahydrofuran), poly(THF), precursor having an azide group, obtained through an electrostatic self-assembly and covalent fixation (ESA-CF) process, and complementary tetrafunctional alkyne ...

Monitoring lipid distribution and metabolism in cells and biological fluids poses many challenges because of the many molecular species and metabolic pathways that exist. This study describes the synthesis and study of molecules that contain an alkyne functional group as surrogates for natural lipids in cultured cells. Thus, hexadec-15-ynoic and hexadec-7-ynoic acids were readily incorporated i...

Herein we describe the sequential synthesis of a variety of azide-alkyne click chemistry-compatible heterobifunctional oligo(ethylene glycol) (OEG) linkers for bioconjugation chemistry applications. Synthesis of these bioorthogonal linkers was accomplished through desymmetrization of OEGs by conversion of one of the hydroxyl groups to either an alkyne or azido functionality. The remaining dista...

The coupling reaction mechanisms of the Rh(iii)-catalyzed redox-neutral C7-selective aryl C-H functionalization of indolines with alkynes and alkenes have been theoretically investigated with the aid of the density functional theory (DFT) calculations. Our calculation results indicate that the active catalyst in this system is the cationic species [Cp*Rh(OAc)]+ (2cat) instead of the neutral spe...

We have prepared a range of alkynyl benzoates in high yields and have investigated their reactivities with the strong Lewis acid B(C6F5)3. In such molecules both σ-activation of the carbonyl and π-activation of the alkyne are possible. In contrast to the reactivity of propargyl esters with B(C6F5)3 which proceed via 1,2-addition of the ester and B(C6F5)3 across the alkyne, the inclusion of an a...

Triphenylsilanolate ligands were found to impart excellent reactivity and outstanding functional group tolerance on molybdenum alkylidyne complexes, which catalyze alkyne metathesis reactions of all sorts. The active species either can be obtained in high yield by adaptation of the established synthesis routes leading to Schrock alkylidynes or can be generated in situ from the molybdenum nitrid...

Herein the examination of transformation alkynes by low-coordinate iron silylamides is presented. An anionic linear iron(I) ([Fe(N{Dipp}SiR3)2]−; Dipp=2,6-di-iso-propylphenyl, R=Me) acts as precatalyst for cyclotrimerization diphenyl acetylene but unable to transform internal with aliphatic substituents or terminal accordingly. For a benzylic, alkyne, however, 1,3-H-shift alkyne observed and pr...

Developing tools for investigating the cellular activity of glycans will help to delineate the molecular basis for aberrant glycosylation in pathological processes such as cancer. Metabolic oligosaccharide engineering, which inserts sugar-reporting groups into cellular glycoconjugates, represents a powerful method for imaging the localization, trafficking, and dynamics of glycans and isolating ...

Stable ruthenium nanoparticles protected by 1-octynyl fragments were synthesized by a wet chemical method. Transmission electron microscopic measurements showed that the resulting particles exhibited an average core diameter of 2.55 ( 0.15 nm with well-defined Ru crystalline lattice fringes. Because of the formation of RusCt bonds, the CtC vibrational stretch was found in FTIR measurements to r...