Solvent-catalyzed umpolung carbonsulfur bond-forming reactions by nucleophilic addition of thiolate and sulfinate ions to in situ–derived nitrosoalkenes in deep eutectic solvents | Zendy

Giuseppe Dilauro | Zendy; Luciana Cicco | Zendy; Filippo Maria Perna | Zendy; Paola Vitale | Zendy; Vito Capriati | Zendy

Open Access

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

Author(s) -

Giuseppe Dilauro,

Luciana Cicco,

Filippo Maria Perna,

Paola Vitale,

Vito Capriati

Publication year - 2017

Publication title -

comptes rendus chimie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.653

H-Index - 76

eISSN - 1878-1543

pISSN - 1631-0748

DOI - 10.1016/j.crci.2017.01.008

Subject(s) - umpolung , chemistry , nucleophile , anhydrous , choline chloride , catalysis , yield (engineering) , solvent , organic chemistry , deep eutectic solvent , in situ , counterion , eutectic system , ion , materials science , alloy , metallurgy

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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