Potassium xanthate-promoted reductive sulfuration reaction: from aldehydes to thiol, disulfide, and thioester derivatives

Feng, Yingqi; Nie, Jinli; Xie, Sijie; He, Ziqing; Hong, Huanliang; Li, Jian; Huang, Yubing; Chen, Lu; Li, Yibiao

doi:10.1039/d3cc05637f

Cited by 2 publications

(2 citation statements)

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“…To the best of our knowledge, the sole attempt to directly transform xanthates into dialkyl thioethers was reported by Degani et al They obtained only small amounts of the desired dialkyl thioethers via the sulfurization of alkyl halides using EtOCS 2 K as a sulfurizing agent [ 38 ]. Based on our research on the development of xanthate chemistry ( Scheme 1 d–f) [ 39 , 40 , 41 ], we herein report a facile approach for use in generating various dialkyl thioethers and aryl thioethers. This approach involves the sulfuration of alkyl halides and aryl halides using ROCS 2 K as a thiol-free sulfurizing and alkylating reagent ( Scheme 1 g).…”

Section: Introductionmentioning

confidence: 99%

Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents

Nie,

He,

Xie

et al. 2024

Molecules

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Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most of the methods for synthesis alkyl thioethers employ foul-smelling thiols as starting materials or generate them as by-products. Additionally, most thiols are air-sensitive and are easily oxidized to produce disulfides under atmospheric conditions; thus, a novel method for synthesizing thioethers is necessary. This paper reports a simple, effective, green method for synthesizing dialkyl or alkyl aryl thioether derivatives using odorless, stable, low-cost ROCS2K as a thiol surrogate. This transformation offers a broad substrate scope and good functional group tolerance with excellent selectivity. The reaction likely proceeds via xanthate intermediates, which can be readily generated via the nucleophilic substitution of alkyl halides or aryl halides with ROCS2K under transition-metal-free and base-free conditions.

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Section: Introductionmentioning

confidence: 99%

Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents

Nie,

He,

Xie

et al. 2024

Molecules

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“…The synthesis of alkyl–alkyl sulfides has traditionally relied on substitution reactions of alkyl halides with mercaptans and thiol–ene additions of alkenes with mercaptans . However, these methods have certain drawbacks.…”

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confidence: 99%

Iodine-Promoted Reductive Sulfenylation Using Ketones as Hydride Donors

Duan,

Guo,

Zheng

et al. 2024

J. Org. Chem.

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Herein, an iodine-promoted reductive sulfenylation reaction of ketones with disulfides has been developed. This method provides an approach for synthesizing unsymmetrical alkyl−alkyl and alkyl−aryl sulfides in a single step. Investigation of the reaction mechanism revealed that ketones play a dual role in this process. They react with disulfides to produce vinyl thioethers and act as effective organic hydride donors, reducing the number of vinyl thioethers that are formed in situ. This study expands the range of applications of ketones in chemical synthesis.

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Potassium xanthate-promoted reductive sulfuration reaction: from aldehydes to thiol, disulfide, and thioester derivatives

Abstract: Herein, aiming to develop a synthetic strategy for the direct construction of C–S bonds to obtain sulfur-containing biologically active compounds, a methodology involving the reductive sulfuration of aldehydes or ketones...

Cited by 2 publications

References 38 publications

Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents

Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents

Iodine-Promoted Reductive Sulfenylation Using Ketones as Hydride Donors

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