Oxidation of disulfides with Selectfluor™: concise syntheses of thiosulfonates and sulfonyl fluorides

Kirihara, Masayuki; Naito, Sayuri; Ishizuka, Yuki; Hanai, Honoka; Noguchi, Takuya

doi:10.1016/j.tetlet.2011.03.132

Cited by 74 publications

(32 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…12 Kirihara et al reported a method to transform disulfides and thiols into sulfonyl fluorides using Selectfluor and refluxing conditions. 13 Despite the synthetic value of these approaches, the use of costly and atom-inefficient fluoride sources limits their practicality to small scale applications.…”

mentioning

confidence: 99%

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

et al. 2019

View full text Add to dashboard Cite

Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based “click chemistry” is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.

show abstract

mentioning

confidence: 99%

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

et al. 2019

View full text Add to dashboard Cite

show abstract

“…The classical chloride‐fluoride exchange of arenesulfonyl chlorides for the synthesis of corresponding arenesulfonyl fluorides requires preparation of arenesulfonyl chlorides that are relatively unstable and moisture‐sensitive (Scheme 1A). [ 1,3 ] Alternative starting materials including ArSO 2 NHNH 2 , [ 4 ] ArSO 2 Na, [ 5 ] ArSO 3 Na, [ 6 ] ArSSAr, [ 7 ] ArSH, [ 8 ] etc ., have been successfully converted into the desired corresponding arenesulfonyl fluorides using an appropriate oxidant and fluorinating reagents (Scheme 1A). An efficient synthesis of various arenesulfonyl fluorides by palladium‐catalyzed cross‐coupling of aryl halides with 1,4‐diazabicyclo[2.2.2]octane‐bis(sulfur dioxide) adduct (DABSO) in combination with electrophilic fluorinating reagents has been developed recently (Scheme 1B).…”

Section: Background and Originality Contentmentioning

confidence: 99%

Arenesulfonyl Fluoride Synthesis via Copper‐free Sandmeyer‐type Fluorosulfonylation of Arenediazonium Salts

Lin

Zheng

et al. 2020

Chin. J. Chem.

View full text Add to dashboard Cite

Summary of main observation and conclusion The limited availability of highly valuable arenesulfonyl fluorides seriously hinders their further application in many research fields including medicinal chemistry and chemical biological, organic synthesis, polymer preparation, etc. We report herein a mild and efficient copper‐free Sandmeyer‐type fluorosulfonylation reaction of various arenediazonium salts to prepare valuable arenesulfonyl fluorides using K2S2O5 as both a reductant and a practical sulfonyl source in combination with N‐fluorobenzenesulfonimide as an effective fluorine source. This methodology provides an attractive route to diverse important arenesulfonyl fluorides given the overall practicality and scope.

show abstract

“…The thiophenolic functionality was found to be more unstable towards 1 than its phenolic analogues and could be readily transformed to disulfides and further to sulfonates [ 22 ], and this path was accepted as a methodology for concise synthesis of thiosulfonates. Symmetric aromatic or benzylic disulfides 17 were thus efficiently transformed to thiosulfonates 18 with a 2.5 fold molar excess of 1 in aqueous MeCN [ 27 ], while alkyl phenyl sulfides under these reaction conditions with an equimolar amounts of 1 gave selectively the sulfoxide functionality [ 28 ].…”

Section: Functionalizations Of Organic Compounds With Sementioning

confidence: 99%

Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis

Stavber

2011

Molecules

View full text Add to dashboard Cite

SelectfluorTM F-TEDA-BF4 (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2.2.2]octane bis(tetrafluoroborate) is not only one of the most efficient and popular reagents for electrophilic fluorination, but as a strong oxidant is also a convenient mediator or catalyst of several “fluorine-free” functionalizations of organic compounds. Its applications as a mediator in transformations of oxidizable functional groups or gold-catalyzed C-C and C-heteroatom oxidative coupling reactions, a catalyst in formation of various heterocyclic rings, a reagent or catalyst of various functionalizations of electron-rich organic compounds (iodination, bromination, chlorination, nitration, thiocyanation, sulfenylation, alkylation, alkoxylation), a catalyst of one-pot-multi-component coupling reactions, a catalyst of regioselective ring opening of epoxides, a deprotection reagent for various protecting groups, and a mediator for stereoselective rearrangement processes of bicyclic compounds are reviewed and discussed.

show abstract

Oxidation of disulfides with Selectfluor™: concise syntheses of thiosulfonates and sulfonyl fluorides

Cited by 74 publications

References 42 publications

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride

Arenesulfonyl Fluoride Synthesis via Copper‐free Sandmeyer‐type Fluorosulfonylation of Arenediazonium Salts

Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis

Contact Info

Product

Resources

About