Pd-G3 XantPhos Mediated Approach to Bis-arylsulfenyl-benzo-2,1,3-thiadiazoles under Microwave Irradiation in DMF: Synthesis and Fluorescent Properties

Ramesh Katla; Rakhi Katla; Eliézer Quadro Oreste; Felipe Kessler

doi:10.1055/a-1958-4406

Synthesis, Table of Contents

Synthesis 2023; 55(05): 799-807
DOI: 10.1055/a-1958-4406

paper

Pd-G3 XantPhos Mediated Approach to Bis-arylsulfenyl-benzo-2,1,3-thiadiazoles under Microwave Irradiation in DMF: Synthesis and Fluorescent Properties

Authors

Ramesh Katla ∗

^aOrganic Chemistry Laboratory-IV, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil
Rakhi Katla

^bOrganic Catalysis and Biocatalysis Laboratory – LACOB, Federal University of Grande Dourados-UFGD, Dourados/MS, Brazil
Eliézer Quadro Oreste

^cLaboratory of Applied and Technological Physical Chemistry, School of Chemistry and Food, Federal University of Rio Grande, Av. Itália, km 8, Rio Grande, RS, Brazil
Felipe Kessler

^cLaboratory of Applied and Technological Physical Chemistry, School of Chemistry and Food, Federal University of Rio Grande, Av. Itália, km 8, Rio Grande, RS, Brazil

Abstract

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Abstract

Synthesis of bis-arylsulfenyl-benzo-2,1,3-thiadiazoles was accomplished using a Pd-G3 XantPhos as a simple and inexpensive catalyst. Numerous benzene thiols reacted well with 4,7-dibromo-benzo-2,1,3-thiadiazole in DMF, using K₂CO₃ as the base, obtaining high product yields in a short reaction time. All the synthesized compounds showed remarkable fluorescence properties with emission wavelengths in the visible range. Due to their unique properties, these compounds have potential for application as image probes in fluorescence microscopy. The study found that these compounds have a wide range of potential uses in the area of sensors, as well as displaying other useful photophysical properties.

Key words

cross-coupling - XantPhos-PdG3 - MWI - DMF - photophysical properties - homogeneous catalysis

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References

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Supplementary Material

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