The low transition temperature mixture formed by lactic acid and choline chloride proved to be effective for an umpolung carbon. sulfur bond formation at the α-position of α-chloro oximes. Aliphatic, aromatic, and heteroaromatic thiolate and sulfinate ions can be smoothly added to in situ-derived nitrosoalkenes affording the corresponding sulfenylated or sulfonylated adducts, respectively, in a very good yield (up to >98%). This methodology offers the advantage of working at room temperature and under air in biodegradable and cost-effective reaction mixtures, which can be used both as solvents and catalysts (20 mol %), thereby avoiding the use of anhydrous, hazardous volatile organic solvents and an inert atmosphere.

Solvent-catalyzed umpolung carbon-sulfur bond-forming reactions by nucleophilic addition of thiolate and sulfinate ions to in situ-derived nitrosoalkenes in deep eutectic solvents

DILAURO, GIUSEPPE;CICCO, LUCIANA;PERNA, FILIPPO;VITALE, PAOLA;CAPRIATI, Vito
2017-01-01

Abstract

The low transition temperature mixture formed by lactic acid and choline chloride proved to be effective for an umpolung carbon. sulfur bond formation at the α-position of α-chloro oximes. Aliphatic, aromatic, and heteroaromatic thiolate and sulfinate ions can be smoothly added to in situ-derived nitrosoalkenes affording the corresponding sulfenylated or sulfonylated adducts, respectively, in a very good yield (up to >98%). This methodology offers the advantage of working at room temperature and under air in biodegradable and cost-effective reaction mixtures, which can be used both as solvents and catalysts (20 mol %), thereby avoiding the use of anhydrous, hazardous volatile organic solvents and an inert atmosphere.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/183466
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