- Method for preparing thioether from unsaturated olefin without catalysis of transition metal
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The invention relates to a synthetic method for preparing thioether by a reaction of unsaturated olefin and thiophenol without catalysis of transition metal. The synthetic method comprises the following steps: adding an unsaturated olefin substrate and a thiophenol substrate into a reaction tube, then adding a catalytic amount of tripentafluorophenyl boron, and carrying out a reaction at 30-80 DEGC for 1-24 hours so as to obtain a thioether compound. Main innovation points of the invention are as follows: the thioether compound can be efficiently prepared without using of a transition metal catalyst, so heavy metal pollution is avoided. The method provided by the invention has the advantages of greenness, no solvent, simple and convenient operation, mild conditions, rapid reaction, good substrate universality, high reaction yield and selectivity and the like.
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Paragraph 0029-0030
(2020/05/11)
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- Few-layer Black Phosphorous Catalyzes Radical Additions to Alkenes Faster than Low-valence Metals
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The substitution of catalytic metals by p-block main elements has a tremendous impact not only in the fundamentals but also in the economic and ecological fingerprint of organic reactions. Here we show that few-layer black phosphorous (FL-BP), a recently
- Tejeda-Serrano, María,Lloret, Vicent,Márkus, Bence G.,Simon, Ferenc,Hauke, Frank,Hirsch, Andreas,Doménech-Carbó, Antonio,Abellán, Gonzalo,Leyva-Pérez, Antonio
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p. 2226 - 2232
(2020/03/04)
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- C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
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An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.
- Xuan, Maojie,Lu, Chunlei,Lin, Bo-Lin
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supporting information
(2019/08/26)
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- Photooxidation of alkyl 4-nitrophenyl sulfides and sulfoxides. Observation of oxidative C-S bond cleavage and rearrangement reactions
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Alkyl 4-nitrophenyl sulfides and sulfoxides undergo a self-photoinduced, singlet oxygen oxidation to produce a variety of products, including sulfonates and carbonyl compounds formed by the oxidative cleavage of the C-S bond of the sulfides and sulfoxides. Structural rearrangements are observed in the resulting carbonyl compounds formed in the oxidative cleavage of the C-S bond in the tert-amyl and 2-phenylethyl sulfides. An overall mechanism is proposed which involves the formation of peroxysulfoxides and peroxysulfones which undergo heterolytic C-S bond cleavage to form ion pairs which recombine to form persulfenates or persulfinates which then undergo photo- and/or thermallyinduced homolytic O-O bond cleavage to form alkoxy and sulfinyl or sulfonyl radicals. The alkoxy radicals undergo β-scission, disproportionation, or recombination with the sulfonyl radical to form the observed products. These C-S oxidative cleavage reactions have only been rarely observed in the earlier studies on the singlet oxygen oxidation studies of dialkyl sulfides, and are attributed, in part, to the presence of the 4-nitro group on the aromatic ring which greatly affects the susceptibility of the sulfur atom of the sulfides and sulfoxides toward nucleophilic attack, and on the reactivity of the peroxysulfoxides and peroxysulfones toward heterolytic cleavage of the O-S bond.
- Pasto, Daniel J.,Cottard, Fran?ois,Jumelle, Laurent
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p. 8978 - 8984
(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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- Arylisothiocyanate for the regulation of plant growth
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New arylisothiocyanates corresponding to the formula STR1 wherein R represents alkyl, alkoxy or halogen X represents oxygen or sulfur and P represents an integer of from 2 to 5 are disclosed. They can be used for the regulation of plant growth especially for the dessication and defoliation of unlignified parts of plants above the soil.
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