26826-81-3Relevant articles and documents
Synthesis of Enhanced, Isolable Disulfanium Salts and their Application to Thiiranium-Promoted Polyene Cyclizations
Cole, Charles J. F.,Chi, Hyung Min,Debacker, Kenneth C.,Snyder, Scott A.
, p. 4351 - 4358 (2018)
Although electrophile-promoted polyene cyclizations have long been a mainstay transformation for the rapid and stereocontrolled preparation of varied natural products and designed molecules, efforts to effect sulfur-promoted variants have arguably lagged behind other counterparts. This state of affairs is particularly true with alkyl sulfide-based electrophiles, even in racemic variants. Herein, building on previously reported discoveries, is described a distinct and modular method to prepare a range of isolable alkyl and aryl disulfanium salts that can affect thiiranium-based polyene cyclizations in moderate to good yields. In most of the substrates probed, these reagents provide superior yields to previously reported alternatives. In addition, initial efforts to develop an asymmetric variant of the process through the use of chiral versions of these reagents are discussed.
Intramolecular Chalcogenylation of Isooxazolines Mediated by PhICl 2and Diorganyl Disulfides or Diselenides
Zhang, Dongke,Zhang, Jingran,Li, Xiaoxian,Yu, Zhenyang,Li, Yadong,Sun, Fengxia,Du, Yunfei
, p. 411 - 420 (2021/10/05)
Reactive organosulfenyl chlorides (ArSCl) or selenenyl chlorides (ArSeCl), generated in situ from the reaction of PhICl 2with diorganyl disulfides or diselenides, enable the intramolecular oxidative cyclization/chalcogenylation of β,γ-unsaturated oximes, leading to the formation of a series of chalcogenylated isooxazolines in good to excellent yield.
Trichloroisocyanuric acid-promoted thiolation of phosphites by thiols
Chen, Yingying,Li, Meichao,Gong, Zhangshui,Shen, Zhenlu
, p. 19 - 27 (2020/08/06)
A simple and convenient method for the synthesis of thiophosphates by coupling of phosphites with thiols under mild conditions has been developed. The reactions were promoted by trichloroisocyanuric acid (TCCA) and were carried out at room temperature in
In Situ Formation of RSCl/ArSeCl and Their Application to the Synthesis of 4-Chalcogenylisocumarins/Pyrones from o-(1-Alkynyl)benzoates and (Z)-2-Alken-4-ynoates
Xing, Linlin,Zhang, Yong,Li, Bing,Du, Yunfei
supporting information, p. 3620 - 3624 (2019/05/24)
The reaction of diorganyl disulfides or diselenides with PhICl2 in acetonitrile was found for the first time to lead to the in situ formation of organosulfenyl chloride or selenenyl chloride, which enables the regioselective intramolecular chalcogenylacyloxylation of alkynes resulting in the formation of 4-chalcogenylisocumarins/pyrones in good to excellent yields under metal-free conditions.
Controlled chemical release of hydrogen sulfide
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Page/Page column 17, (2015/09/22)
Agents of formula: where R1 and R2 vary independently and are acyl, sulfonyl, phosphoryl, alkyl, substituted alkyl, halogen, aryl, arylalkyl, substituted aryl, heteroaryl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, heterocycle, or heteroatoms; and R3 is H or a member of a ring structure which includes R2, are provided; as are agents of formula: where R1, R2 and R3 vary independently and: R1=OH, OR′, NHR′, NR′R″ (with R′ R″=alkyl, aryl, heteroaryl, etc); R2=acyl, alkyl, aryl, sulfonyl, etc; R3=alkyl, aryl, substituted aryl, heteroaryl, etc; and R4 and R5 are (independently) H, methyl or alkyl, substituted alkyl, aryl, substituted aryl, etc. Methods of using the agents to treat e.g. cardiovascular disease, stroke, shock, injuries caused by hypoxia, male erectile dysfunction, and Alzheimer's are provided.
Diaryl and heteroaryl sulfides: Synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents
Yonova, Ivelina M.,Osborne, Charlotte A.,Morrissette, Naomi S.,Jarvo, Elizabeth R.
, p. 1947 - 1953 (2014/04/03)
A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
Synthesis of aryl thioethers through the N -chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents
Cheng, Jun-Hao,Ramesh, Chintakunta,Kao, Hsin-Lun,Wang, Yu-Jen,Chan, Chien-Ching,Lee, Chin-Fa
, p. 10369 - 10374 (2013/01/15)
A convenient one-pot approach for the synthesis of aryl sulfides through the coupling of thiols with Grignard reagents in the presence of N-chlorosuccinimide is described. The sulfenylchlorides were formed when thiols were treated with N-chlorosuccinimide, and the resulting sulfenylchlorides were then directly reacted with Grignard reagents to provide aryl sulfides in good to excellent yields under mild reaction conditions. Functional groups including ester, fluoro, and chloro are tolerated by the reaction conditions employed. It is important to note that this method has a short reaction time (30 min in total) and represents an alternative approach for the synthesis of aryl sulfides over the existing protocols.
[[(tert-Butyl)dimethylsilyl]oxy]-methylGroup for sulfur protection
Wang, Lihong,Clive, Derrick L. J.
supporting information; experimental part, p. 1734 - 1737 (2011/06/09)
Aromatic and aliphatic thiols can be protected by reaction with t-BuMe 2SiOCH2Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe2SiOCH2SR or t-BuMe2SiOCH2SAr are deprotected by sequential treatment with Bu4NF and I2 to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined with Me(CH2) 11SCH2OSiMe2Bu-t and three sulfenyl chlorides.
Preparation of sulfenyl pyrroles
Gillis, H. Martin,Greene, Lana,Thompson, Alison
experimental part, p. 112 - 116 (2009/06/18)
Sulfenyl groups are attracting interest as masking/protecting groups for pyrroles. A facile one-step synthesis of sulfenyl pyrroles, involving the reaction of pyrroles with N-(aryl- and alkylthio)phthalimides in the presence of MgBr2, is reported and the methodology extends to include sulfinyl pyrroles. The one-step procedure gives good yields and is more efficient and practical than current multistep protocols to sulfenyl pyrroles that involve thiocyanato pyrrolic intermediates. A convenient procedure for the synthesis of N-(aryl- and alkylthio)phthalimides is also reported. Georg Thieme Verlag Stuttgart.
Synthesis and reactivity of fluorine-containing thiols and thioacyl halides
Sizov,Kovregin,Serdyuk,Vorob'ev,Porosyatnikov,Tsvetkov,Korneev,Ermolov
, p. 1200 - 1208 (2008/02/02)
A route to α-hydropolyfluoroalkanethiols and polyfluorothioacyl halides via thermal splitting of benzyl polyfluoroalkyl sulfides under the action of phosphorus pentoxide was proposed. The thiols obtained were used as starting materials for the synthesis of α-hydropolyfluoroalkanesulfenyl chlorides. The properties of the resulting F,S-containing compounds were studied. Springer Science+Business Media, Inc. 2006.
