Photocatalytic Three-Component Reaction for the Synthesis of Multifunctional Diaryl Sulfides.

J Org Chem

School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, PR China.

Published: December 2023

A photocatalytic three-component reaction of a nitroarene, a thiophenol, and a ketone for the synthesis of multifunctional diaryl sulfides was reported using a nitro group as the nitrogen source and thiophenol as the sulfur source. Thiophenol also serves as a proton donor to reduce nitroarene to arylamine as a key intermediate for the formation of C-N and C-S bonds. Good functional group tolerance and mild reaction conditions make this method have practical synthetic value for diversified multifunctional diaryl sulfides.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.3c02048DOI Listing

Publication Analysis

Top Keywords

multifunctional diaryl
12
diaryl sulfides
12
photocatalytic three-component
8
three-component reaction
8
synthesis multifunctional
8
source thiophenol
8
reaction synthesis
4
sulfides photocatalytic
4
reaction nitroarene
4
nitroarene thiophenol
4

Similar Publications

Recently, transition metal-catalyzed ortho-C-H bond activation/annulations involving two internal alkyne molecules have been extensively used to synthesize highly substituted polycyclic aromatic scaffolds. Such reactions have emerged as a powerful atom and step-economical strategy for the assembly of multifunctional bioactive molecules. In this context, we focused on the recent achievements of dual C-H bond activation/annulations, as well as functionalization reactions involving diaryl/alkyl alkynes.

View Article and Find Full Text PDF

Stable Anion Exchange Membrane Bearing Quinuclidinium for High-performance Water Electrolysis.

Angew Chem Int Ed Engl

May 2024

Center of Artificial Photosynthesis for Solar Fuels and Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, 310030, Zhejiang Province, China.

Anion exchange membranes (AEMs) are core components in anion exchange membrane water electrolyzers (AEM-WEs). However, the stability of functional quaternary ammonium cations, especially under high temperatures and harsh alkaline conditions, seriously affects their performance and durability. Herein, we synthesized a 1-methyl-3,3-diphenylquinuclidinium molecular building unit.

View Article and Find Full Text PDF

Targeted Library of Phosphonic-Type Inhibitors of Human Neutrophil Elastase.

Molecules

March 2024

Division of Organic and Medicinal Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland.

Despite many years of research, human neutrophil elastase (HNE) still remains an area of interest for many researchers. This multifunctional representative of neutrophil serine proteases is one of the most destructive enzymes found in the human body which can degrade most of the extracellular matrix. Overexpression or dysregulation of HNE may lead to the development of several inflammatory diseases.

View Article and Find Full Text PDF

Photocatalytic Three-Component Reaction for the Synthesis of Multifunctional Diaryl Sulfides.

J Org Chem

December 2023

School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, PR China.

A photocatalytic three-component reaction of a nitroarene, a thiophenol, and a ketone for the synthesis of multifunctional diaryl sulfides was reported using a nitro group as the nitrogen source and thiophenol as the sulfur source. Thiophenol also serves as a proton donor to reduce nitroarene to arylamine as a key intermediate for the formation of C-N and C-S bonds. Good functional group tolerance and mild reaction conditions make this method have practical synthetic value for diversified multifunctional diaryl sulfides.

View Article and Find Full Text PDF

Disclosed herein is a novel and efficient synthesis of dapagliflozin and canagliflozin, the most advanced sodium glucose cotransporter 2 inhibitors (SGLT2 inhibitors), for the treatment of type 2 diabetes mellitus (T2DM). Per Ac-protected thioester was prepared by the treatment of per Ac d-gluconolactone with 1-dodecanethiol and PrMgCl without affecting labile Ac-protecting groups. Aryl bromide (ArBr) was synthesized through reduction of diaryl ketone to diaryl methane by the TiCl/NaBH/DME-MeOH reduction system.

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!