Oxidation of <i>N</i>-trifluoromethylthio sulfoximines using NaOCl·5H<sub>2</sub>O

Testen, Žan; Jereb, Marjan

doi:10.1039/d3ob02033a

Cited by 3 publications

(1 citation statement)

References 66 publications

(53 reference statements)

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“…A report from the group of Harmata described one example of the preparation of N -sulfinyl sulfoximine from sulfonyl chloride and NH-sulfoximine . Recently, the synthesis of N -trifluoromethylthio sulfoximines by oxidation is described . Establishing generic protocols for the synthesis of N -sulfinyl sulfoximines holds considerable importance for the synthetic chemistry community.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-Sulfinyl Sulfoximines from 5-(Sulfoximido)dibenzothiophenium Triflates and Sodium Sulfinates

Wei,

Zhao,

et al. 2024

J. Org. Chem.

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A transition-metal-free and efficient S−O/S−N bond interconversion reaction has been developed. The protocol facilitates an efficient synthesis of N-sulfinyl sulfoximines by reacting sulfoximido-substituted sulfonium salts with a wide range of sodium sulfinates, featuring broad substrate scope, including a plethora of heterocyclic and fluoroalkyl substrates, high functional group tolerance, and mild conditions.

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Section: Introductionmentioning

confidence: 99%

Synthesis of N-Sulfinyl Sulfoximines from 5-(Sulfoximido)dibenzothiophenium Triflates and Sodium Sulfinates

Wei,

Zhao,

et al. 2024

J. Org. Chem.

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Photocatalytic Hydrogenation of Alkenes Using Water as Both the Reductant and the Proton Source

Tian,

Qiu,

et al. 2024

Advanced Science

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Utilization of clean and low‐cost water as the reductant to enable hydrogenation of alkenes is highly attractive in green chemistry. However, this research subject is considerably challenging due to the sluggish kinetics of the water oxidation half‐reaction. It is also very difficult to avoid the undesired oxidation of alkenes because that this oxidation is far easier to occur than the desired oxidation of water from thermodynamic standpoint. Herein, this challenge is overcome by applying a cooperative catalysis where HCl is used as the cocatalyst to accelerate Pt/g‐C3N4‐catalyzed water oxidation and suppress the undesired oxidation of the alkene. This provides an example for using water as the reductant and the proton source to enable the photocatalytic hydrogenation of alkenes. The present method exhibits broad substrate applicability, and allows various arylethenes and aliphatic alkenes to undergo the hydrogenation smoothly.

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Strategies for oxidative synthesis of N-triflyl sulfoximines

Testen,

Jereb

2024

RSC Adv.

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Oxidation of N-trifluoromethylthio sulfoximines using NaOCl·5H₂O

Abstract: N-trifluoromethylthio sulfoximines are biologically interesting compounds, but their potential is still poorly understood. The oxidation of N-trifluoromethylthio sulfoximines led to their corresponding sulfoxide derivatives as a new type of compound,...

Cited by 3 publications

References 66 publications

Synthesis of N-Sulfinyl Sulfoximines from 5-(Sulfoximido)dibenzothiophenium Triflates and Sodium Sulfinates

Synthesis of N-Sulfinyl Sulfoximines from 5-(Sulfoximido)dibenzothiophenium Triflates and Sodium Sulfinates

Photocatalytic Hydrogenation of Alkenes Using Water as Both the Reductant and the Proton Source

Strategies for oxidative synthesis of N-triflyl sulfoximines

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Oxidation of N-trifluoromethylthio sulfoximines using NaOCl·5H2O

Abstract: N-trifluoromethylthio sulfoximines are biologically interesting compounds, but their potential is still poorly understood. The oxidation of N-trifluoromethylthio sulfoximines led to their corresponding sulfoxide derivatives as a new type of compound,...

Cited by 3 publications

References 66 publications

Synthesis of N-Sulfinyl Sulfoximines from 5-(Sulfoximido)dibenzothiophenium Triflates and Sodium Sulfinates

Synthesis of N-Sulfinyl Sulfoximines from 5-(Sulfoximido)dibenzothiophenium Triflates and Sodium Sulfinates

Photocatalytic Hydrogenation of Alkenes Using Water as Both the Reductant and the Proton Source

Strategies for oxidative synthesis of N-triflyl sulfoximines

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Product

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About

Oxidation of N-trifluoromethylthio sulfoximines using NaOCl·5H₂O