A Thiol-Free Route to Alkyl Aryl Thioethers

Bugaenko, Dmitry I.; Volkov, A.; Карчава, А. В.

doi:10.1021/acs.joc.3c00734

Cited by 4 publications

(2 citation statements)

References 32 publications

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“…2 thiol surrogates in nucleophilic substitution or cross-coupling with aryl halides in synthesising aryl thioethers (Scheme 1a-b). Karchava et al described the visible-light-driven S-arylation of EtOCS2K (Et = ethyl) using aryl halides in synthesising aryl thioethers [36], followed by the reaction of diaryliodonium salts with xanthate salts to prepare the corresponding alkyl aryl thioether compounds (Scheme 1c) [37]. Nevertheless, xanthates, which are generally used as thiol surrogates, react with aryl halides to generate aryl thioethers, but the synthesis of dialkyl thioethers using xanthates has rarely been reported.…”

Section: Introductionmentioning

confidence: 99%

Expedient Syntheses of Alkyl and Aryl Thioethers using Xanthates as Thiol-Free Reagents

Nie,

He,

Xie

et al. 2024

Preprint

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Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most of the methods for synthesizing 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 Syntheses of Alkyl and Aryl Thioethers using Xanthates as Thiol-Free Reagents

Nie,

He,

Xie

et al. 2024

Preprint

View full text Add to dashboard Cite

show abstract

“…Baranov [ 34 ] and Kakulapati [ 35 ] reported the use of xanthates as thiol surrogates in nucleophilic substitution or cross-coupling with aryl halides in synthesizing aryl thioethers ( Scheme 1 a,b). Karchava et al described the visible-light-driven S-arylation of EtOCS 2 K (Et = ethyl) using aryl halides in synthesizing aryl thioethers [ 36 ], followed by the reaction of diaryliodonium salts with xanthate salts to prepare the corresponding alkyl aryl thioether compounds ( Scheme 1 c) [ 37 ]. Nevertheless, xanthates, which are generally used as thiol surrogates, react with aryl halides to generate aryl thioethers, but the synthesis of dialkyl thioethers using xanthates has rarely been reported.…”

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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Arylation of Diethyl Acetamidomalonate with Diaryliodonium Salts En Route to α-Arylglycines

Bugaenko,

Tikhanova,

Andreychev

et al. 2024

J. Org. Chem.

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Diethyl acetamidomalonate (DEAM) has been widely used for the synthesis of α-amino acids via C-alkylation under basic conditions followed by hydrolysis/decarboxylation. In contrast, the C-arylation of this reagent remains undeveloped. Herein, we report a novel strategy for the synthesis of racemic αarylglycines based on the selective arylation of DEAM with diaryliodonium salts under mild, transition metal-free conditions. The reaction features good functional group tolerance and easy scalability and is applicable to the chemoselective C−H-modification of arenes including approved drugs, thus enabling a straightforward approach to complex α-arylglycines that would be challenging to make otherwise.

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A Thiol-Free Route to Alkyl Aryl Thioethers

Cited by 4 publications

References 32 publications

Expedient Syntheses of Alkyl and Aryl Thioethers using Xanthates as Thiol-Free Reagents

Expedient Syntheses of Alkyl and Aryl Thioethers using Xanthates as Thiol-Free Reagents

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

Arylation of Diethyl Acetamidomalonate with Diaryliodonium Salts En Route to α-Arylglycines

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