A one-pot three-component reaction using p-quinone methides, rongalite and alkyl/allyl halides has been described. The corresponding unsymmetrical sulfones were obtained in good yields under mild reaction conditions in the absence of any metal, base or any other additive.
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http://dx.doi.org/10.1002/asia.202200408 | DOI Listing |
RSC Adv
December 2023
Chemistry Department, College of Sciences, Shiraz University Shiraz Iran +98 7136460788 +98 7136137107.
A novel green Cu(ii)-acidic deep eutectic solvent (Cu(ii)-ADES) bearing copper salt, choline chloride, and gallic acid ([ChCl][2GA-Cu(ii)]) was synthesized and thoroughly specified by physicochemical approaches such as FT-IR, EDX, XRD, Mapping, ICP, and UV-Vis analyses and physicochemical properties. After the detection of authentic data, the central composite design (CCD) was utilized to accomplish the pertaining tests and develop the optimum condition, and, in the following, [ChCl][2GA-Cu(ii)] was applied as a green multifunctional catalytic solvent system in reducing agent-free and base-free condition for the three-component click reaction from sodium azide, alkyl, allyl, ester, and benzyl halide, and terminal alkyne made from amines and caprolactam as a cyclic amide to furnish a successful new library of 1,4-disubstituted 1,2,3-triazoles with a yield of up to 98%. The Cu(ii)-ADES is stable and can comfortably be recovered and reused without a considerable decline in its acting for seven cycles.
View Article and Find Full Text PDFACS Org Inorg Au
August 2022
Department of Chemistry, Queen Mary University of London, Mile End Road, London E1 4NS, U.K.
A highly efficient, cost-effective, and environmentally friendly protocol is reported for the C5-selective alkylation of hydantoins under phase-transfer catalysis. The reactions are scalable and only require a catalytic amount of tetrabutylammonium bromide (TBAB) to achieve high yields under mild reaction conditions. Moreover, the method is applicable to a wide range of electrophiles, including alkyl-, allyl-, propargyl-, and benzyl halides, as well as acrylates and dibromoalkanes, but also to virtually any hydantoin precursor.
View Article and Find Full Text PDFChem Asian J
August 2022
Division of Organic Chemistry, CSIR - National Chemical Laboratory, 411008, Pune, India.
A one-pot three-component reaction using p-quinone methides, rongalite and alkyl/allyl halides has been described. The corresponding unsymmetrical sulfones were obtained in good yields under mild reaction conditions in the absence of any metal, base or any other additive.
View Article and Find Full Text PDFMolecules
May 2021
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.
The efficient synthesis of a new family of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes in high yields has been developed based on 9-selenabicyclo[3.
View Article and Find Full Text PDFOrg Lett
March 2019
CNRS, UMR 5253, AM2N , Institut Charles Gerhardt Montpellier ENSCM , 8 rue de l'École Normale , F-34296 Montpellier Cedex 5 , France.
An α-vinylation of enolizable ketones has been developed by using β-bromostyrenes and a KO tBu/NMP system. β,γ-Unsaturated ketones of E configuration were obtained in excellent yield and selectivity. Further synthetic possibilities are highlighted by one-pot functionalization via trapping of intermediate dienolates with alkyl, allyl, benzyl, and propargyl halides to generate quaternary centers.
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