Synthesis and applications of thiosulfonates and selenosulfonates as free-radical reagents

Wang, Xin; Meng, Jianping; Zhao, Dongyang; Tang, Shi; Sun, Kai

doi:10.1016/j.cclet.2022.08.016

Cited by 54 publications

(50 citation statements)

References 115 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among the organosulfur compounds, the derivatives with unique SS bonds are particularly important due to their vast applications; the family includes: disulfides, 7,8 thiosulfinates 9,10 and thiosulfonates. 11,12 In this regard, the protocols that install a new SS bond is synthetically very important. Among SS bond containing molecules, thiosulfonates -also known as the S-esters of thiosulfonic acid and sulfonothioates-are a special class, where one of the sulfur of the SS bond is a dioxide, i.e., SO2, and the other one is a simple sulfide.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Thiols with IBX or DMP: One-pot Access to Thiosulfonates or 2-Iodobenzoates and Applications in Functional Group Transformations

Chandra

Yadav

Payra³

et al. 2023

Preprint

View full text Add to dashboard Cite

Thiosulfonates are accessed by oxidation of feed-stock thiols using either DMP in DCM or IBX in MeCN at rt (~30 degree C). The protocol gives access to a variety of thiosulfonates in good to excellent yields from both aromatic and aliphatic thiols. The reaction with DMP is found to be better than IBX in terms of reaction rate and conversion, whereas the oxidation with DMP requires lower equivalent than IBX. Benzyl thiols are however found to follow a different reaction pathway when treated with DMP; O-benzyl esters of o-iodobenzoates were isolated. The 1H NMR spectroscopic monitoring studies for the IBX-mediated oxidation of thiol found disulfide as an initial intermediate, which is proposed to undergoes a cascade of oxidations to produce thiosulfonate

show abstract

Section: Introductionmentioning

confidence: 99%

Oxidation of Thiols with IBX or DMP: One-pot Access to Thiosulfonates or 2-Iodobenzoates and Applications in Functional Group Transformations

Chandra

Yadav

Payra³

et al. 2023

Preprint

View full text Add to dashboard Cite

show abstract

“…Organosulfur and organoselenium compounds play an increasingly important role in organic synthesis and material science as well as in pharmaceutical applications [ 1 ]. In particular, C–S bonds exist in numerous natural products and biological and pharmaceutical compounds, such as nelfinavir, esomeprazole, and cephalosporin-type antibiotics, most of which have demonstrated antibacterial, antiviral, antitumor, and anti-inflammatory activities [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology

et al. 2023

Self Cite

View full text Add to dashboard Cite

Dichalcogenides (disulfides and diselenides), as reactants for organic transformations, are important and widely used because of their potential to react with nucleophiles, electrophilic reagents, and radical precursors. In recent years, in combination with photochemical technology, the application of dichalcogenides as stable radical reagents has opened up a new route to the synthesis of various sulfur- and selenium-containing compounds. In this paper, synthetic strategies for disulfides and diselenides and their applications with photochemical technology are reviewed: (i) Cyclization of dichalcogenides with alkenes and alkynes; (ii) direct selenylation/sulfuration of C−H/C−C/C−N bonds; (iii) visible-light-enabled seleno- and sulfur-bifunctionalization of alkenes/alkynes; and (iv) Direct construction of the C(sp)–S bond. In addition, the scopes, limitations, and mechanisms of some reactions are also described.

show abstract

“…In this review, we will focus on the recent advances on thiolation mainly involving classic sulfur electrophiles as well as the comprehensive mechanisms on these developments. It should be noted that the electrophilic fluoromethylthiolating reagents 13 and the radical type thiolation with thiolating reagents 14 are not included in this review.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in thiolation via sulfur electrophiles

et al. 2022

View full text Add to dashboard Cite

show abstract

Synthesis and applications of thiosulfonates and selenosulfonates as free-radical reagents

Cited by 54 publications

References 115 publications

Oxidation of Thiols with IBX or DMP: One-pot Access to Thiosulfonates or 2-Iodobenzoates and Applications in Functional Group Transformations

Oxidation of Thiols with IBX or DMP: One-pot Access to Thiosulfonates or 2-Iodobenzoates and Applications in Functional Group Transformations

Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology

Recent advances in thiolation via sulfur electrophiles

Contact Info

Product

Resources

About