Activated by visible light, arylazo sulfones can serve as multifaceted reactants and are employed in diazenylation, sulfonylation, and arylation reactions under (photo)catalyst-free conditions. Such versatile reactivity enabled us to develop an operationally simple, regioselective, and tunable difunctionalization of styrenes with arylazo sulfones to produce α-sulfonyl arylhydrazones and 1,2-alkoxyarylated products in moderate to excellent yields. Furthermore, such difunctionalized products have been exploited as key building blocks for the synthesis of various heterocycles.
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http://dx.doi.org/10.1021/acs.orglett.3c03786 | DOI Listing |
J Org Chem
December 2024
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Botanic Garden, Howrah 711103, India.
Herein, we describe a Zn-catalyzed atom-economical, inexpensive, and sustainable method for preparing a broad spectrum of substituted olefins utilizing alcohols as the main precursor. Using a Zn(II) complex [ZnLCl] () of the redox-noninnocent ligand 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (), various ()-olefins were prepared in good yields by coupling alcohols with sulfones and aryl cyanides under an inert atmosphere. Under an aerial atmosphere, vinyl nitriles were isolated in up to 82% yield reacting alcohols with benzyl cyanides in the presence of .
View Article and Find Full Text PDFNanoscale Adv
August 2024
Istituto per la Sintesi Organica e la Fotoreattività (ISOF), Consiglio Nazionale delle Ricerche (CNR) Via P. Gobetti, 101 40129 Bologna Italy
Covalent functionalization of graphene presents a pivotal strategy to enhance its surface properties and overcome inherent chemical inertness. While diazonium salts have been extensively utilized for this purpose, their limitations necessitate exploration of alternative approaches. Arylazo sulfones, such as diazonium salt derivatives serving as chromophores, offer a promising solution, enabling photochemical reactions under visible light.
View Article and Find Full Text PDFChemistry
November 2024
Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo (FCFRP-USP), Av. do Café, s/n° - Campus Universitário da USP, 14040-903, Ribeirão Preto/SP, Brazil.
BODIPYs have a well-established role in biological sciences as chemosensors and versatile biological markers due to their chemical reactivity, which allows for fine-tuning of their photophysical characteristics. In this work, we combined the unique reactivity of arylazo sulfones with the advantages of a "sunflow" reactor to develop a fast, efficient, and versatile method for the photochemical arylation of BODIPYs and other chromophores. This approach resulted in red-shifted emitting fluorophores due to extended electronic delocalization at the 3- and 5-positions of the BODIPY core.
View Article and Find Full Text PDFChem Asian J
April 2024
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology., 200 Xiao Ling Wei Street, Nanjing, 210094, China.
A highly efficient new protocol has been developed for the formation of C-Te bonds, leading to both symmetrical and unsymmetrical diaryl tellurides. This protocol utilizes sodium aryltellurites (4), which can be easily prepared from low-cost aryltelluride trichlorides and NaOH. The synthesis involves the use of 4 and arylazo sulfones as starting materials in the presence of (MeO)P(O)H.
View Article and Find Full Text PDFOrg Biomol Chem
January 2024
Polymer Research Laboratory, Department of Chemistry, Motilal Nehru National Institute of Technology Allahabad, Prayagraj 211004, India.
The photochemical action of arylazo sulfones under visible light irradiation has recently gained considerable attention for the construction of carbon-carbon and carbon-heteroatom bonds in organic synthesis. The inherent dyedauxiliary group (-NSOR) embedded in the reagent is responsible for the absorption of visible light even in the absence of a photocatalyst, additive or oxidant, leading to the generation of three different radicals, . aryl (carbon-centred), sulfonyl (sulphur-centred) and diazenyl (nitrogen-centred) radicals, under different reaction conditions.
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