Multicomponent synthesis of sulfonamides from triarylbismuthines, nitro compounds and sodium metabisulfite in deep eutectic solvents

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Title: Multicomponent synthesis of sulfonamides from triarylbismuthines, nitro compounds and sodium metabisulfite in deep eutectic solvents
Authors: Marset, Xavier | Torregrosa-Crespo, Javier | Martínez-Espinosa, Rosa María | Guillena, Gabriela | Ramón, Diego J.
Research Group/s: Alternative Methodologies In Chemistry (AMIC) | Bioquímica Aplicada/Applied Biochemistry (AppBiochem) | Catálisis Estereoselectiva en Síntesis Orgánica (CESO)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Departamento de Agroquímica y Bioquímica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Synthesis | Sulfonamides | Triarylbismuthines | Nitro compounds | Sodium metabisulfite | Deep eutectic solvents
Knowledge Area: Química Orgánica | Bioquímica y Biología Molecular
Issue Date: 3-Jul-2019
Publisher: Royal Society of Chemistry
Citation: Green Chemistry. 2019, 21: 4127-4132. doi:10.1039/C9GC01541H
Abstract: A sustainable synthesis of sulfonamides using a copper-catalysed process starting from triarylbismuthines, Na2S2O5 and nitro compounds in a Deep Eutectic Solvent (DES) as a reaction medium is described. Thus, triarylbismuthines are used as reagents for the incorporation of SO2 into organic motifs. The bismuth salts formed as by-products can be easily removed from the crude reaction mixture by precipitation with water, while the use of volatile organic compounds (VOCs) as solvents can be avoided in the entire process. The eutectic mixture employed as the solvent is fully characterised, with the preliminary results proving its low toxicity. The designed DES also allows for a novel multicomponent reaction which saves time and reduces purification steps, energy and cost.
Sponsor: This work was supported by the University of Alicante (VIGROB-173 and VIGROB-309) and the Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P and PGC2018-096616-B-I00). X. M. and J. T. C. thank Generalitat Valenciana (ACIF/2016/057 and ACIF/2016/077) for their fellowships.
URI: http://hdl.handle.net/10045/94932
ISSN: 1463-9262 (Print) | 1463-9270 (Online)
DOI: 10.1039/C9GC01541H
Language: eng
Type: info:eu-repo/semantics/article
Rights: © The Royal Society of Chemistry 2019
Peer Review: si
Publisher version: https://doi.org/10.1039/C9GC01541H
Appears in Collections:INV - CESO - Artículos de Revistas
INV - AMIC - Artículos de Revistas
INV - AppBiochem - Artículos de Revistas

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