An efficient synthetic route for the construction of -aryl 1,2,3-triazoles is reported via sequential C-N bond formation and electro-oxidative N-N coupling under metal-free conditions. Readily accessible 2-aminoacrylates and aryldiazonium salts were used as starting materials, and the developed protocol displays excellent functional group tolerance, allowing an extensive range of substrate scope up to 91% isolated yield. Various mechanistic studies, along with the isolation of an intermediate adduct, refer to successive ionic and radical reaction sequences.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.1c04099DOI Listing

Publication Analysis

Top Keywords

-aryl 123-triazoles
8
aryldiazonium salts
8
regioselective synthesis
4
synthesis -aryl
4
123-triazoles electro-oxidative
4
electro-oxidative coupling
4
coupling enamines
4
enamines aryldiazonium
4
salts efficient
4
efficient synthetic
4

Similar Publications

In this study, a novel hybrid nanostructure consisting of acid-decorated chitosan and magnetic AlFeO nanoparticles was fabricated. The acid-decorated chitosan provided a stable and biocompatible matrix for the magnetic AlFeO nanoparticles. Various techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction patterns (XRD), thermogravimetric analysis (TGA), vibrating sample magnetometry (VSM), specific surface area (BET), scanning electron microscopy (SEM), and energy-dispersive X-ray spectroscopy (EDS) were used to characterize and confirm the successful synthesis of the hybrid nanostructure.

View Article and Find Full Text PDF

DNDMH enabled C(sp)-H nitration of aryl alkenes.

Chem Commun (Camb)

January 2025

School of Chemistry & Material Science, Northwest University, 1st Xuefu Avenue, Xi'an, Shaanxi 710127, China.

C(sp)-H bond nitration provides facile access to nitro compounds that are inaccessible through traditional nitration pathways. This work describes a C(sp)-H bond nitration of aryl alkenes using DNDMH, a nitration reagent developed previously in our lab. Notably, this novel nitration process presents excellent regioselectivity and chemoselectivity between C(sp)-H nitration and C(sp)-H nitration.

View Article and Find Full Text PDF

Environmental and population influences on mummichog () gut microbiomes.

Microbiol Spectr

January 2025

Marine Chemistry & Geochemistry Department, Woods Hole Oceanographic Institution, Woods Hole, Massachusetts, USA.

Unlabelled: The mummichog, , an abundant estuarine fish broadly distributed along the eastern coast of North America, has repeatedly evolved tolerance to otherwise lethal levels of aromatic hydrocarbon exposure. This tolerance is linked to reduced activation of the aryl hydrocarbon receptor (AHR) signaling pathway. In other animals, the AHR has been shown to influence the gastrointestinal-associated microbial community, particularly when activated by the model toxic pollutant 3,3',4,4',5-pentachlorobiphenyl (PCB-126) and other dioxin-like compounds.

View Article and Find Full Text PDF

On the reactivity of complexes [Ni(NHC)] with CS.

Dalton Trans

January 2025

Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.

A study of the reaction of [Ni(NHC)] synthons with the heterocumulene CS is reported. Nickel complexes of η-(C-S) coordinated CS, [Ni(NHC)(η-CS)] (NHC = IiPr (1a), IiPr (1b)) were obtained from the reaction of CS with precursors of [Ni(NHC)] (NHC = IiPr, IiPr). The result of this reaction critically depends on the NHC employed, as [Ni(IMes)], the complex of the sterically more demanding -aryl substituted NHC IMes, led to formation of the dinuclear complex [{Ni(IMes)(μ-CS)}] (2d).

View Article and Find Full Text PDF

Mechanochromic materials, known for their ability to change color in response to mechanical stimuli such as pressure, stretching, grinding, or rubbing, hold significant importance due to their diverse applications. In this study, we synthesized and characterized two novel pyridine-tethered imidazo[1,2-a]pyridine mechanoresponsive luminogens with appended tetraphenylethene, named GBY-10 and GBY-11. GBY-10 exhibited reversible mechanofluorochromism, while GBY-11 did not revert to its original color after solvent fuming.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!