- Ruthenium-catalyzed decarboxylative C-S cross-coupling of carbonothioate: synthesis of allyl(aryl)sulfide
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A novel ruthenium-catalyzed decarboxylative cross-coupling of carbonothioate is disclosed. This method provides straightforward access to the corresponding allyl(aryl)sulfide derivatives in generally good to excellent yields under mild conditions and feat
- Zheng, Ren-Hua,Guo, Hai-Chang,Chen, Ting-Ting,Huang, Qing,Huang, Guo-Bo,Jiang, Hua-Jiang
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p. 25123 - 25126
(2018/07/29)
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- Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements
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A mild hemin catalytic system for sulfonium ylide generation via a metal carbenoid and a subsequent [2,3]-sigmatropic rearrangement reaction in aqueous solvent is well-established, with the assistance of cyclodextrin (CD) and Triton X-100. The protocol displays high catalytic activity with a broad substrate scope of aryl/alkyl allyl sulfides and diazo reagents, affording homoallyl sulfide products in up to 99% yield. Notably, this catalytic system is successful for water-insoluble allyl sulfides but ineffective for allyl amines or allyl ethers. Moreover, an unprecedented cascade reaction of sulfonium ylide formation, [2,3]-sigmatropic rearrangement and C-H insertion was reported.
- Xu, Xiaofei,Li, Chang,Tao, Zhihao,Pan, Yuanjiang
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supporting information
p. 1245 - 1249
(2017/08/15)
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- Nickel-Schiff base complex catalyzed C-S cross-coupling of thiols with organic chlorides
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We report an efficient, mild and convenient synthetic protocol for the C-S cross-coupling reaction of various aryl, benzyl, allyl chlorides and thiols using 5 mol % Nickel-Schiff base catalyst with NaOH as the base, in DMF at 70 °C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available organic chlorides and thiols.
- Gogoi, Prasanta,Hazarika, Sukanya,Sarma, Manas J.,Sarma, Kuladip,Barman, Pranjit
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p. 7484 - 7489
(2014/12/10)
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- Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides
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A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.
- Pace, Vittorio,Castoldi, Laura,Holzer, Wolfgang
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supporting information; experimental part
p. 967 - 972
(2012/03/11)
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- Sulfite-promoted one-pot synthesis of sulfides by reaction of aryl disulfides with alkyl halides
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A sodium dithionite, sodium thiosulfate and rongalite promoted one-pot synthesis of aryl alkyl sulfides at room temperature has been developed. The reactions of a range of disulfides with alkyl halides proceeded smoothly in the presence of rongalite. Possible reaction pathways are discussed and the effects of these sulfites on disulfides are investigated. The important features of this protocol are metal-free, strong-base-free, and mild reaction conditions, operational simplicity, short reaction times and high yields of products. Georg Thieme Verlag Stuttgart.
- Tang, Ri-Yuan,Zhong, Ping,Lin, Qiu-Lian
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- One-pot synthesis of sulfides by reaction of disulfides with alkyl halides in the presence of sodium dithionite
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Sodium dithionite-promoted synthesis of unsymmetrical diorganyl sulfides by a reaction of diaryl disulfides with alkyl halides at r.t. has been developed. The advantages offered by this method are operational simplicity, a faster reaction, neutral and mild reaction conditions, and moderate to good yields of products.
- Tang, Ri-Yuan,Zhong, Ping,Lin, Qiu-Lian
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p. 167 - 174
(2007/10/03)
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- CsF-Celite, an efficient solid state reagent for the syntheses of thioesters and thioethers
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Coupling reactions of a number of aliphatic, aromatic, and heterocyclic compounds bearing an acidic hydrogen atom attached to sulfur, with alkyl, acyl, benzyl, or benzoyl halides in acetonitrile with cesium fluoride-Celite are described. This procedure is convenient, efficient, and practical for the preparation of thioethers and thioesters. Springer-Verlag 2005.
- Shah, Syed T. A.,Khan, Khalid M.,Hussain, Hidayat,Hayat, Safdar,Voelter, Wolfgang
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p. 1583 - 1589
(2007/10/03)
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- An alternative approach towards the syntheses of thioethers and thioesters using CsF-Celite in acetonitrile
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It has been found that syntheses of thioethers and thioesters of aliphatic, aromatic and heterocyclic compounds, bearing thiol groups, can be accomplished with alkyl, acyl, benzyl or benzoyl halides in acetonitrile and cesium fluoride-Celite. In this manner, compounds like ethanethiol, 1-pentanethiol, thiophenol, 4-methoxythiophenol, 4-nitrothiophenol, and 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, and 2-mercapto-2-thiazoline can be successfully alkylated, acylated, benzylated or benzoylated. This procedure is convenient, efficient and practical for the preparation of thioethers and thioesters.
- Shah, Syed Tasadaque Ali,Khan, Khalid Mohammed,Martinez Heinrich, Angelica,Voelter, Wolfgang
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p. 8281 - 8283
(2007/10/03)
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- The synthesis of allyl sulfides by organosamarium reagent
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Organosamarium reagent reacts with disulfides to afford allyl sulfides in THF.
- Yu, Mingxin,Zhang, Yongmin
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p. 2743 - 2748
(2007/10/03)
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- A Study of the Regioselectivity of the Radical Addition of "RSAr" Derived from the Photolysis of tert-Homoallyl and tert-Alkyl 4-Nitrobenzenesulfenates to Substituted Allenes and Alkenes
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The regioselectivity of the free radical addition of "RSAr" derived from the photolysis of tert-homoallyl and tert-alkyl 4-nitrobenzenesulfenates, followed by β-scission of the alkoxy radicals to produce the allyl or alkyl radicals R., to 1,1- and 1,3-dimethylallene and acrylonitrile and methyl acrylate has been determined.The regioselectivity of addition of "RSAr" to 1,1- and 1,3-dimethylallene occurs by the addition of the arylthiyl radical to the center carbon atom of the allene chromophore, whereas the regioselectivity of the addition to acrylonitrile and methyl acrylate varies with the nature of the R..The results are interpreted in terms of the relative reactivities of the ? systems toward radical addition and the relative rates of β-scission of the intermediate alkoxy radicals versus the rates of addition of the 4-nitrobenzenethiyl radical and R. to the ? systems.
- Pasto, Daniel J.,Cottard, Francois
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p. 4642 - 4646
(2007/10/02)
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- Photolysis of Alkyl 4-Nitrobenzenesulfenates. A New and Versatile Method for the Generation of Free Radicals
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The irradiation of alkyl 4-nitrobenzenesulfenates with >300-nm wavelength light in benzene solution results in the homolytic cleavage of the O-S bond.The tertiary alkoxy radicals thus formed undergo β scission to produce carbon-centered free radicals in e
- Pasto, Daniel J.,L'Hermine, Gael
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p. 5815 - 5816
(2007/10/02)
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- The use of aminoiminomethanesulfinic acid (thiourea dioxide) under phase transfer conditions for generating organochalcogenate anions. Synthesis of sulfides, selenides and tellurides
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A procedure is described which allows for the in situ synthesis of arylalkyl, diaryl and dialkylchalcogenides under phase transfer conditions starting from the corresponding diorganodichalcogenides.The dichalcogenides are reduced by aminoiminomethanesulfinic acid (thiourea dioxide) in alkaline medium and catalyzed by a quaternary ammonium salt.The reduction proceeds easily for diaryl disulfides and diaryl diselenides at a sodium hydroxide concentration of 13percent; diaryl ditellurides require a 50percent sodium hydroxide solution to give the aryl tellurolate anion.The dialkyl diselenides and dialkyl ditellurides are more difficult to reduce.The intermediate arylthiolates and arylselenolates are quenched by alkyl and activated aryl halides to give the corresponding sulfides and selenides in high yield (77-97percent).The aryltellurolates react with alkyl halides giving the aryl alkyl tellurides in 81-96percent yield.The procedure could not be successfully used for the synthesis of dialkylselenides and dialkyl tellurides; low yields and mixture of products were formed.
- Comasseto, J. V.,Lang, E. S.,Ferreira, J. Tercio B.,Simonelli, F.,Correira, V. R.
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p. 329 - 340
(2007/10/02)
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- Nucleophilic Aromatic Substitution with Thiolate Ions Under Solid-Liquid Phase Transfer Conditions
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A convenient synthesis of aryl alkyl sulphides under solid-liquid phase transfer conditions (using triethylbenzylammonium chloride as catalyst and solid KOH) (TEBA/KOH) from aryl halides and thiolate ions generated in situ from thioiminium salts, is described.
- Singh, Paramjit,Batra, Manohar S.,Singh, Harjit
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p. 729 - 730
(2007/10/02)
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- STRUCTURAL EFFECTS UPON COMPETITIVE DECOMPOSITION PATHWAYS OF THIOSULFOXIDE INTERMEDIATES
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Mixtures of sulfides and disulfides are obtained upon reaction of boron trisulfide with a series of allyl aryl sulfoxides, with the product distributions dependent upon the structures of the intermediate thiosulfoxides.
- Baechler, Raymond D.,Filippo, Lynn James San,Schroll, Alayne
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p. 5247 - 5250
(2007/10/02)
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- Regio- and Stereo-selectivity in the Reactions of Anions of Aryl Allyl Sulfides with Benzaldehyde
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Addition reactions of anions of aryl allyl sulfides to benzaldehyde proceed readily and in good yields and afford mixtures of products resulting from α- and γ-attack on the allyl anion. γ-Products predominate, and the ratio of (E):(Z) isomers usually surrounds unity, although in the case of the reaction involving 3-(phenylthio)but-1-ene the ratio is 10:1.The ratio of diastereoisomers formed in products resulting from α-attack ranges from 3:1 to 1.3:1 (starting from 3-(2,4,6-trimethyl-phenylthio)prop-1-ene and 2-methyl-3-(phenylthio)prop-1-ene respectively).
- Ridley, Damon D.,Smal, Mary A.
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p. 1345 - 1355
(2007/10/02)
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