Hypervalent Iodine in Synthesis XXIII: Oxidation with [Hydroxy(tosyloxy)iodo]benzene: Selective Oxidation of Sulfides to Sulfoxides

doi:10.1080/00397919708006059

Paper

Hypervalent Iodine in Synthesis XXIII: Oxidation with [Hydroxy(tosyloxy)iodo]benzene: Selective Oxidation of Sulfides to Sulfoxides

Published Apr 1, 1997 · M. Xia, Zhenchu Chen

Synthetic Communications

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Abstract

Abstract Alkyl-and aryl-sulfides can be selectively oxidated to their corresponding sulfoxides with excellent yields under mild conditions by [hydroxy (tosyloxy)iodo]benzene. Morever, [hydroxy (((+)-10-camphorosulfonyl)oxy)iodo]benzene as the chiral oxidizer, can be used to oxidate unsymmetric sulfides to sulfoxides with a few %ee to some extent.

Study Snapshot

Selective oxidation of alkyl- and aryl-sulfides to sulfoxides with excellent yields under mild conditions by [hydroxy (tosyloxy)iodo]benzene offers a promising method for synthesis of chiral iodides.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Hypervalent Iodine in Synthesis XXIII: Oxidation with [Hydroxy(tosyloxy)iodo]benzene: Selective Oxidation of Sulfides to Sulfoxides

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References

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Oxaziridine is a highly stereoselective reagent for oxidation of sulphides to chiral sulphoxides, allowing the preparation of several chiral -sulphinyl aldehydes under mild reaction conditions.

Citations

Direct Synthesis of Sulfinylated Phenanthrenes via BF3-Promoted Annulation of 2-Alkynyl Biaryls with Arylsulfinic Acids.

This novel approach enables the synthesis of various sulfinylated phenanthrenes in good to excellent yields under simple and mild reaction conditions using readily available arylsulfinic acids.

Chiral Hypervalent Iodines: Active Players in Asymmetric Synthesis.

Chiral hypervalent iodines (III/V) have revolutionized asymmetric synthesis due to their nontoxic, environmentally friendly, and high stability, enabling unprecedented enantioselective transformations.

Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones

Hypervalent iodine reagents efficiently catalyze regioselective cycloaddition of enaminones with nitrile oxides, resulting in moderate to good yields of 3,4-disubstituted isoxazoles.

Visible-light-activated selective synthesis of sulfoxides via thiol-ene/oxidation reaction cascade

This study presents a metal-free, highly selective, and eco-friendly method for synthesising sulfoxides from alkenes and thiols using visible light and air, yielding up to 96% yields at room temperature.

Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes.

The developed oxidative cyclization method efficiently produces heterobicyclic phospholene oxides and isoxazoline-ring-fused heterobicyclic products in moderate to good yields.

Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant

Visible-light photoredox catalysis using inexpensive Rose Bengal and air as green oxidants enables the facile and practical construction of sulfoxides from alkenes and thiols.

Chiral Hypervalent Iodine(III) Catalyst Promotes Highly Enantioselective Sulfonyl- and Phosphoryl-oxylactonizations.

This enantioselective oxylactonization of 4-pentenoic acids enables the production of a wide range of sulfonyloxy- and phosphoryloxy--butyrolactones with respectable yields and moderate to excellent enantiose

Phenyliodine Bis(trifluoroacetate) (PIFA) as an Excellent Promoter of 2-Deoxy-2-phthalimido-1-thioglycosides in the Presence of Triflic Acid in Glycosylation Reactions

Phenyliodine bis(trifluoroacetate) (PIFA) and trifluoromethanesulfonic acid effectively promote glycosylation reactions, enabling the synthesis of D-glucosamine or D-galactosamine-containing disaccharides.