- Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants
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A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (KEDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.
- Cai, Yi-Ping,Nie, Fang-Yuan,Song, Qin-Hua
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p. 12419 - 12426
(2021/09/02)
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- Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries
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Functionalized α-oximinoketones with β-alkoxy, β-alkyl, and β-sulfenyl groups were used as efficient synthons for the preparation of chiral 1-acyl-4-imidazolin-2-ones and 1-acylimidazolidin-2-ones. For the preparation of the former heterocycles, α-oximinoketones were transformed into their respective imidazole N-oxides by neutral treatment with a chiral triazine, followed by reaction with acetic or propionic anhydrides to furnish the desired chiral 1-acetyl- or 1-propionyl-4-imidazolin-2-ones in moderate overall yields. Upon palladium hydroxide-catalyzed hydrogenation, these series were converted into their corresponding 1-acylimidazolidin-2-ones in high diastereoisomeric ratios. Thus, these novel chiral 1-acetyl- and 1-propionyl-imidazolidin-2-ones were obtained with a variety of alkyl groups at the C-4 and C-5 positions of the heterocycle, through a three-step methodology, and can be applied as new potential chiral auxiliaries.
- Gutiérrez, Rsuini U.,Rebollar, Araceli,Bautista, Rafael,Pelayo, Vanessa,Várgas, José Luis,Montenegro, Mabel M.,Espinoza-Hicks, Carlos,Ayala, Francisco,Bernal, Pablo M.,Carrasco, Cuauhtemoc,Zepeda, L. Gerardo,Delgado, Francisco,Tamariz, Joaquín
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p. 230 - 246
(2015/03/04)
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- Indium(I) iodide promoted cleavage of dialkyl disulfides - Application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides
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Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding β-ketosulfides or β-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding β-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably fast. Thus, simple and convenient procedures for the synthesis of β-ketosulfides or β-cyanosulfides and β-hydroxyalkyl sulfides have been developed using this cleavage reaction.
- Ranu, Brindaban C.,Mandal, Tanmay
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p. 762 - 770
(2007/10/03)
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- Synthesis of novel β-functionalized α-oximinoketones via hetero-Michael addition of alcohols and mercaptans to enones
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A new methodology has been developed for the preparation of β-alkoxy and β-sulfenyl ketones by hetero-Michael addition of the corresponding alcohols and thiols to enones under acidic and basic conditions. The direct conversion of enones into β-alkoxy and
- Bernal, Pablo,Tamariz, Joaquín
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p. 2905 - 2909
(2007/10/03)
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- Study of the Michael addition of β-cyclodextrin-thiol complexes to conjugated alkenes in water
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An environmentally benign and highly efficient supramolecular Michael addition of thiols from the secondary side of β-cyclodextrin to α,β-unsaturated compounds at the primary side in water is described in quantitative yields; products of undesirable side
- Krishnaveni, N. Srilakshmi,Surendra,Rao, K. Rama
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p. 669 - 671
(2007/10/03)
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- A simple and green procedure for the conjugate addition of thiols to conjugated alkenes employing polyethylene glycol (PEG) as an efficient recyclable medium
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Polyethylene glycol (PEG) is found to be an inexpensive, nontoxic, environmentally friendly reaction medium for the conjugate addition of thiols to conjugated alkenes to afford the corresponding adducts in excellent yields under mild and neutral condition
- Kamal, Ahmed,Reddy, D. Rajasekhar,Rajendar
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p. 7951 - 7953
(2007/10/03)
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- Indium(I) iodide-promoted cleavage of dialkyl disulfides and subsequent Michael addition of thiolate anions to conjugated carbonyl compounds
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Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions which then undergo facile addition to α,β-unsaturated ketones, aldehydes, carboxylic esters and nitriles under neutral conditions producing corresponding β-keto or β-cyano
- Ranu, Brindaban C.,Mandal, Tanmay
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p. 1239 - 1242
(2007/10/03)
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