Switchable Synthesis of Aryl Sulfones and Sulfoxides through Solvent-Promoted Oxidation of Sulfides with O/Air.

Org Lett

The Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, School of Chemistry and Chemical Engineering , Xinjiang University, Urumqi 830046 , P.R. China.

Published: November 2019

A practical and switchable method for the synthesis of aryl sulfones and sulfoxides via sulfide oxidation was developed. The chemoselectivities of products were simply controlled by reaction temperature using O/air as the terminal oxidant and oxygen source. The broad substrate scope, easy realization of gram-scale production, and the simplification of a sulfide oxidation system render the strategy attractive and valuable.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.9b03192DOI Listing

Publication Analysis

Top Keywords

synthesis aryl
8
aryl sulfones
8
sulfones sulfoxides
8
sulfide oxidation
8
switchable synthesis
4
sulfoxides solvent-promoted
4
solvent-promoted oxidation
4
oxidation sulfides
4
sulfides o/air
4
o/air practical
4

Similar Publications

Magnesium (Mg) an essential plant nutrient is widespread deficient in the acidic soils of Nilgiris of Tamil nadu, India. The vegetable yield and quality is especially affected due to deficiency of nutrients like Mg. This study investigates soil characteristics and bacterial diversity in the Nilgiris district of Tamil Nadu, India, with respect to Mg deficiency.

View Article and Find Full Text PDF

The selective synthesis of 4-alkyl/aryl-3H-1,2-dithiole-3-thione in THF and water-dependent switchable product ketothioamide is demonstrated. The presented method describes explicitly the synthesis of the extremely rare positional isomer 4-alkyl/aryl-3H-1,2-dithiole-3-thione, a unique structure distinct from another positional isomer, 5-alkyl/aryl-3H-1,2-dithiole-3-thione. The unique umpolung of the nitromethyl group is exploited for solvent selective nucleophilic sulfur and amine addition.

View Article and Find Full Text PDF

We have developed efficacious routes toward the selective synthesis of two classes of compounds such as C-3 amino-methylated indoles and 4-indol-3-yl-methylanilines from the same precursors, namely, indoles and 1,3,5-triazinanes. It is reported that the controlled cleavage of 1,3,5-triazinanes can be effected by heat for the generation of aryl imine motifs, and we observed that the presence of Lewis acid influences the course of these transformations toward different products. The reaction toward indol-3-yl-methylanilines proceeds via a nucleophilic attack of indole to the aryl imine generated from the 1,3,5-triazinanes to form an amino-methylated product which undergoes a Lewis acid mediated Hofmann-Martius-type rearrangement.

View Article and Find Full Text PDF

Palladium-Catalyzed Modular Synthesis of Thiophene-Fused Polycyclic Aromatics via Sequential C-H Activation.

Org Lett

January 2025

Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China.

A palladium-catalyzed Catellani-type [2+2+2] annulation reaction of aryl iodides, bromothiophenes, and norbornadiene, which proceeds via a tandem Heck coupling/double C-H bond activation and retro-Diels-Alder pathway to access thiophene-fused polyaromatics, is reported. The key feature of this protocol represents a NBD/NBE retaining annulation.

View Article and Find Full Text PDF

Synthesis of nonaromatic [16]thiatriphyrin(2.2.1)s.

Org Biomol Chem

January 2025

Department of Chemistry, IIT Bombay, Powai, Mumbai 400076, India.

[16]Thiatriphyrin(2.2.1)s containing one thiophene and two pyrroles connected five -carbons were synthesized by condensing a new precursor, -fused thiatripyrrane, with an appropriate aryl aldehyde in CHCl under acid-catalyzed inert conditions followed by open air oxidation with DDQ.

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!