LAPSE:2023.4621
Published Article
LAPSE:2023.4621
Reduction of Sulfoxides in Multigram Scale, an Alternative to the Use of Chlorinated Solvents
February 23, 2023
In this manuscript, we describe the use of ethyl vinyl ether/oxalyl chloride as the reducing mixture for sulfoxides. The reaction is based on the high electrophilic character of chlorosulfonium salts, formed in situ by the reaction of oxalyl chloride and the sulfoxide. Thereafter, the nucleophilic vinyl ether acts as a chlorine scavenger, affording the corresponding sulfide. The method is applicable on a big scale and may be applied to highly functionalized sulfoxides. Chromatographic purification is only needed in exceptional cases of unstable substrates, and the final sulfide or the corresponding salt is usually obtained after simple evaporation of volatiles. The sole contaminants of this method are carbon dioxide, carbon monoxide and small (five-carbon maximum) aldol products, which are formed during the reaction process.
Keywords
reduction, sulfides, sulfonium salts, sulfoxides
Subject
Suggested Citation
Adarve-Cardona L, Gamba-Sánchez D. Reduction of Sulfoxides in Multigram Scale, an Alternative to the Use of Chlorinated Solvents. (2023). LAPSE:2023.4621
Author Affiliations
Adarve-Cardona L: Laboratory of Organic Synthesis Bio- and Organocatalysis, Chemistry Department, Universidad de Los Andes, Cra. 1 No. 18A-12 Q:305, Bogotá 111711, Colombia [ORCID]
Gamba-Sánchez D: Laboratory of Organic Synthesis Bio- and Organocatalysis, Chemistry Department, Universidad de Los Andes, Cra. 1 No. 18A-12 Q:305, Bogotá 111711, Colombia [ORCID]
Journal Name
Processes
Volume
10
Issue
6
First Page
1115
Year
2022
Publication Date
2022-06-02
Published Version
ISSN
2227-9717
Version Comments
Original Submission
Other Meta
PII: pr10061115, Publication Type: Journal Article
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LAPSE:2023.4621
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doi:10.3390/pr10061115
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Feb 23, 2023
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