4-Nitro-1,2,3-triazoles are crucial precursors for high energy materials, and their practical synthesis is a long-standing problem. Herein, we communicate a mechanochemical route for the selective synthesis of 4-nitro-1,2,3-triazoles via organocatalyzed oxidative [3 + 2] cycloaddition between β-nitrostyrenes and organic azides. Our conditions avoid divergent pathways and permit the retention of the valuable NO group on the product. Nontoxic catalyst, catalyst recyclability, no rigorous solvent-extraction, no toxic byproducts, atmospheric oxygen, and gram-scale synthesis are some of the salient features.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.2c00621DOI Listing

Publication Analysis

Top Keywords

organocatalyzed oxidative
8
mechanochemical access
4
access functional
4
functional clickates
4
clickates nitro-retentive
4
nitro-retentive selectivity
4
selectivity organocatalyzed
4
oxidative azide-olefin
4
azide-olefin cycloaddition
4
cycloaddition 4-nitro-123-triazoles
4

Similar Publications

The carboamination of unsaturated molecules using bifunctional reagents is considered an attractive approach for the synthesis of nitrogen-containing compounds. However, bifunctional C-N reagents have never been employed in the carboamination of cyclopropane. In this study, we use an N-heterocyclic carbene (NHC), N-benzoyl saccharin, as a bifunctional reagent and a photoredox catalyst for a dual-catalyzed 1,3-aminoacylation of cyclopropane.

View Article and Find Full Text PDF

An Expedient Route to Bio-Based Polyacrylate Alternatives with Inherent Post-Chemical Modification and Degradation Capabilities by Organic Catalysis for Polymerization of Muconate Esters.

Angew Chem Int Ed Engl

December 2024

Laboratoire de Chimie des Polymères Organiques (LCPO), Université de Bordeaux, CNRS, Bordeaux INP, UMR 5629, 16 av. Pey Berland, 33607, Pessac cedex, France.

The quest for polymers that would be at the same time bio-based and degradable after usage, in addition to offering chemical post-modification options, remains a daunting challenge in contemporary polymer science. Despite advances in polymer chemistry, attempts at controlling the chain-growth polymerization of muconate esters remain unexplored. Here we show that dialkyl muconates can be rapidly polymerized by organocatalyzed group transfer polymerization (O-GTP).

View Article and Find Full Text PDF

Organocatalyzed Carbonylation of Alkyl Halides Driven by Visible Light.

Angew Chem Int Ed Engl

December 2024

Department of Chemistry, Colorado State University, Center Ave, Fort Collins, CO 80523, United States.

Herein, we describe a new strategy for the carbonylation of alkyl halides with different nucleophiles to generate valuable carbonyl derivatives under visible light irradiation. This method is mild, robust, highly selective, and proceeds under metal-free conditions to prepare a range of structurally diverse esters and amides in good to excellent yields. In addition, we highlight the application of this activation strategy for C isotopic incorporation.

View Article and Find Full Text PDF

Atroposelective Construction of Axially Chiral 2-Aryl-Pyrroloquinolones.

Org Lett

August 2024

Université Paris-Saclay, UVSQ, CNRS, UMR 8180 Institut Lavoisier de Versailles, 78035 Versailles Cedex, France.

A two-step protocol including an enantioselective organocatalyzed synthesis of pyrroloquinolines followed by an oxidation reaction allowed the formation of axially chiral 2-aryl-pyrroloquinolones. Thorough optimization of the experimental conditions for the second step allowed the oxygenation reaction to take place and ensured, in most cases, a central-to-axial chirality conversion with complete retention of the enantiomeric excess.

View Article and Find Full Text PDF

Organocatalyzed atom transfer radical polymerization (O-ATRP) is a controlled radical polymerization method mediated by organic photoredox catalysts (PCs) for producing polymers with well-defined structures. While -diaryl dihydrophenazine PCs have successfully produced polymers with low dispersity ( < 1.3) in O-ATRP, low initiator efficiencies ( ~ 60-80%) indicate an inability to achieve targeted molecular weights and have been attributed to the addition of radicals to the PC core.

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!