- A direct aldol addition of simple thioesters employing soft enolization
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Simple thioesters undergo direct aldol addition to aldehydes in the presence of magnesium bromide-diethyl ether and N,N-diisopropylethylamine using untreated, reagent grade dichloromethane under atmospheric conditions. The reactions proceed extremely rapi
- Zhou, Guoqiang,Yost, Julianne M.,Coltart, Don M.
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- A facile and efficient direct aldol addition of simple thioesters
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Simple thioesters undergo direct aldol addition to aldehydes in the presence of MgBr2·OEt2 and i-Pr2NEt using untreated, reagent-grade CH2Cl2 under atmospheric conditions. The reactions proceed extrem
- Yost, Julianne M.,Zhou, Guoqiang,Coltart, Don M.
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- NiNP@rGO Nanocomposites as Heterogeneous Catalysts for Thiocarboxylation Cross-Coupling Reactions
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A new type of ligand-free Ni-nanoparticles supported on rGO (size distribution average d = 9 ± 3 nm) was prepared and fully characterized via morphological (Fe-SEM), structural (P-XRD, HR-TEM), and spectroscopic (ICP-EOS, XPS) analysis tools. The metal composite was effectively employed in the unprecedented heterogeneously Ni-assisted cross-coupling reaction of aryl/vinyl iodides and thiocarboxylates. A range of sulfur-containing aryl as well as vinyl derivatives (15 examples) was achieved in high yields (up to 82%), under mild reaction conditions, and with wide functional group tolerance.
- Bandini, Marco,Bertuzzi, Giulio,Gazzano, Massimo,Kovtun, Alessandro,Lombardi, Lorenzo,Mazzaro, Raffaello,Morandi, Vittorio
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- Unsymmetrical Disulfides Synthesis via Cs2CO3-Catalyzed Three-Component Reaction in Water
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An unsymmetrical disulfides synthesis by Cs2CO3-catalyzed three-component coupling reaction of thioacetate, sodium thiosulfate, and benzyl halide in water is described. The safe, stable, and non-toxic Na2S2O3 was invoked as the sulfur-source, successfully avoiding the odor generation in the process of S?S bond formation. A wide range of substrate suitability and appropriate functional group tolerance were observed for the transformation. Notably, the approach reported here was compatible with various biomolecules including glucose, coumarin, and quinolinone. (Figure presented.).
- Wang, Dungai,Gao, Yuanji,Tong, Yunli,Xiong, Mingteng,Liang, Xiao,Zhu, Heping,Pan, Yuanjiang
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supporting information
p. 4991 - 4995
(2020/09/23)
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- Thioesters as Bifunctional Reagents for 2-Naphthylamine Sulfuracylation
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An efficient and convenient strategy for the preparation of diaryl sulfides via a Fe-promoted direct sulfuracylation of 2-naphthylamine using thioesters as bifunctional reagents is described. This synthetic strategy features high chemoselectivity, good substrate scope and functional group tolerance. (Figure presented.).
- Xiao, Fuhong,Yuan, Shanshan,Wang, Dahan,Liu, Saiwen,Huang, Huawen,Deng, Guo-Jun
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supporting information
p. 3331 - 3336
(2019/06/13)
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- S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters
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This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.
- Kuciński, Krzysztof,Hreczycho, Grzegorz
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p. 489 - 493
(2018/04/27)
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- Efficient Cu-catalyzed base-free C-S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides
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S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100°C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the "one-pot" synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.
- Soria-Castro, Silvia M.,Penenory, Alicia B.
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supporting information
p. 467 - 475
(2013/05/08)
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- Aromatic thioether acylation method
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PCT No. PCT/FR96/01763 Sec. 371 Date Aug. 3, 1998 Sec. 102(e) Date Aug. 3, 1998 PCT Filed Nov. 8, 1996 PCT Pub. No. WO97/17324 PCT Pub. Date May 15, 1997The present invention relates to a process for the acylation of an aromatic thioether. In its preferred variant, the invention resides in a process for the condensation of acetic anhydride or acetyl chloride with thioanisole. The process for the acylation of an aromatic thioether according to the invention is characterised in that it consists in reacting said thioether with an acylating agent chosen from the group formed by the halides of carboxylic acids and the anhydrides of carboxylic acids, in the presence of an effective quantity of an acid zeolite.
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