High-surface-area β-MnO2 (β-MnO2-HS) nanoparticles could act as effective heterogeneous catalysts for the one-pot oxidative sulfonamidation of various aromatic and heteroaromatic thiols to the corresponding sulfonamides using molecular oxygen (O2) and ammonia (NH3) as respective oxygen and nitrogen sources, without the need for any additives.
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http://dx.doi.org/10.1039/c9cc09411c | DOI Listing |
Org Biomol Chem
November 2024
Department of Chemistry, Indian Institute of Technology Delhi-110016, New Delhi, India.
In this work, we report a regioselective sulfonamidation of -(2-hydroxyaryl)amides with iminoiodinanes and iodine in visible light at room temperature. The method does not require a strong oxidant, metal or photocatalyst and enables direct functionalization of a C-H bond to a C-N bond. Mechanistic investigations suggest generation of an N-centered radical from ,-diiodo-sulfonamide by homolytic N-I bond cleavage followed by its site-specific addition to -(2-hydroxyaryl)amides to furnish -sulfonamide derivatives.
View Article and Find Full Text PDFJ Org Chem
July 2023
Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM), Dhanbad, Jharkhand 826004, India.
The visible light-triggered regioselective synthesis of 2-sulfonamidoindoles and other 2-sulfonamido heteroarenes is accomplished by the oxidative cross-dehydrogenative coupling of indoles (heteroarenes) with di--toluenesulfonamide or -aryl--toluenesulfonamides. The reaction was catalyzed by eosin-Y through a photoredox route. Detailed mechanistic studies based on control reactions, cyclic voltammetry, and fluorescence quenching have been reported for the elucidation of the mechanistic cycle and revealed that a nitrogen-centered radical is generated, followed by regioselective addition to the heteroarene.
View Article and Find Full Text PDFMolecules
August 2022
Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia.
Among the variety of sulfonamides, triflamides (CFSONHR, TfNHR) occupy a special position in organic chemistry. Triflamides are widely used as reagents, efficient catalysts or additives in numerous reactions. The reasons for the widespread use of these compounds are their high NH-acidity, lipophilicity, catalytic activity and specific chemical properties.
View Article and Find Full Text PDFJ Am Chem Soc
May 2022
Centre for Hyperpolarisation in Magnetic Resonance, Department of Chemistry, University of York, Heslington, York YO10 5DD, U.K.
Here, we show how signal amplification by reversible exchange hyperpolarization of a range of N-containing synthons can be used to enable studies of their reactivity by N nuclear magnetic resonance (NO (28% polarization), ND (3%), PhCHNH (5%), NaN (3%), and NO (0.1%)). A range of iridium-based spin-polarization transfer catalysts are used, which for NO work optimally as an amino-derived carbene-containing complex with a DMAP- coligand.
View Article and Find Full Text PDFRSC Adv
November 2020
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of Russian Academy of Sciences 664033 Irkutsk Russia
Oxidative sulfonamidation of divinylsilanes with various sulfonamides in different solvents is reported. With -BuOI as an oxidant, halogenation is the main process, whereas aziridines are the minor products. With NBS in CHCl the products of bromination or bromosulfonamidation were obtained, whereas in MeCN or THF the Ritter-type solvent interception products are formed.
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