Electrochemical Synthesis of Sulfinic Esters from Alcohols and Thiophenols

He, Ya‐Ling; Yu, Wei; Li, Xu

doi:10.26434/chemrxiv.9945083

Cited by 3 publications

(3 citation statements)

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“…Recently, Zhong and co-workers have reported an electrochemical method for the preparation of sulfinate esters from the reaction of thiols with alcohols (methanol, primary alcohols, and only one example of cyclohexanol) in an undivided electrochemical cell equipped with a platinum anode and a platinum cathode. 19 According to their report, using graphite as an anode electrode has resulted in corresponding sulfinate esters in a much poorer yield, while nickel turned out to be an unsuccessful cathode in the sulfinate ester synthesis. On the other hand, excess of alcohol (near to 10-fold) has been used for the electrochemical synthesis of sulfinate esters.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis of Sulfinate Esters: Nickel(II)-Catalyzed Oxidative Esterification of Thiols with Alcohols in an Undivided Cell

et al. 2020

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In this study, nickel-catalyzed electrochemical oxidative esterification of thiols with alcohols for the synthesis of sulfinate esters has been reported. The electrochemical oxidative esterification proceeded through a nickel-catalyzed oxidation of thiols using an undivided cell of graphite/nickel electrodes, where the nickel oxidation was studied by cyclic voltammetry. The method was conveniently and directly used for the one-pot synthesis of sulfinate esters of thiols.

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Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis of Sulfinate Esters: Nickel(II)-Catalyzed Oxidative Esterification of Thiols with Alcohols in an Undivided Cell

et al. 2020

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“…Racemic and optically active diastereoisomeric and/or enantiomeric sulfinic esters played a very important role in the development of sulfur chemistry and especially sulfur stereochemistry [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ]. Preparation of diastereoisomeric O -menthyl p -toluenesulfinates 2a/3a by reacting p -toluenesulfinyl chloride 1a with (-)-(1 R ,3 S ,5 R )-menthol in the presence of pyridine ( Scheme 1 ) [ 16 ], confirmed for the first time stereogenity of a sulfinyl sulfur atom and its optical stability at room temperature [ 2 , 3 ].…”

Section: Introductionmentioning

confidence: 99%

Diastereoisomerically Pure, (S)-O-1,2-O-isopropyli dene-(5-O-α-d-glucofuranosyl) t-butanesulfinate: Synthesis, Crystal Structure, Absolute Configuration and Reactivity

et al. 2020

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The reaction of t-butylmagnesium chlorides with diastereomerically pure (R)-1,2-O-isopropylidene-3,5-O-sulfinyl-α-d-glucofuranose (R)-4 was found to be stopped at the stage of the corresponding, diastereoisomerically pure 1,2-O-isopropylidene-(5-O-α-d-glucofuranosyl) t-butanesulfinate (S)-10 for which the crystal structure and the (S)-absolute configuration was determined by X-ray crystallography. Comparison of the absolute configurations of the starting sulfite (R)-4, and t-butanesulfinate (S)-10 (which crystallizes in the orthorhombic system, space group P212121, with the single compound molecule present in the asymmetric unit), clearly indicates that the reaction of nucleophilic substitution at the stereogenic sulfur atom in the sulfite (R)-4 occurs with the full inversion of configuration via the trigonal bipyramidal sulfurane intermediate 4c in which both the entering and leaving groups are located in apical positions.

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“…In 2020, Wei and coworkers developed a methodology for the preparation of sulfinate esters via electrochemical process (Scheme 9). 18 This method is a great recent innovation but- In 2018 Hitchcock and coworkers developed a method for sulfinate ester synthesis that utilized 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) with p-toluenesulfinic acid and an alcohol. 20 This method is to be used for the synthesis of the phenoxy sulfinate esters by the addition of a phenol, as seen in Scheme 11.…”

Section: Methodsmentioning

confidence: 99%

The Development Of A New Entry Point Into Enantiomerically Enriched Sulfinyl Derivatives

Shaw¹

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for their guidance in classroom and being always being open for discussions. I would also like to thank Samantha Willens, who taught me the fundamental techniques in the laboratory and making me feel comfortable with doing research. In addition, I would like to think my peers McKenzie Biswell, Ashley Stelmack, Kayla Love, Zain Becerra, and Adrienne Sulit as well as my parents for their moral support and guidance through my graduate career. I would also like to thank the Illinois State University Chemistry Department for fostering such a great environment for learning chemistry. Finally, I

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Electrochemical Synthesis of Sulfinic Esters from Alcohols and Thiophenols

Abstract: Electrochemical oxidative couplings between S–H and O–H bonds are achieved herein directly from readily-available alcohols and thiophenols, affording a series of diverse sulfinic esters.<br>

Cited by 3 publications

References 20 publications

Electrochemical Synthesis of Sulfinate Esters: Nickel(II)-Catalyzed Oxidative Esterification of Thiols with Alcohols in an Undivided Cell

Electrochemical Synthesis of Sulfinate Esters: Nickel(II)-Catalyzed Oxidative Esterification of Thiols with Alcohols in an Undivided Cell

Diastereoisomerically Pure, (S)-O-1,2-O-isopropyli dene-(5-O-α-d-glucofuranosyl) t-butanesulfinate: Synthesis, Crystal Structure, Absolute Configuration and Reactivity

The Development Of A New Entry Point Into Enantiomerically Enriched Sulfinyl Derivatives

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