6633-92-7Relevant academic research and scientific papers
A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent
Anselmi, Silvia,Liu, Siyu,Kim, Seong-Heun,Barry, Sarah M.,Moody, Thomas S.,Castagnolo, Daniele
, p. 156 - 161 (2021/01/14)
A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.
Synthesis of allyl sulfones from potassium allyltrifluoroborates
Stikute, Agnese,Lugi?ina, Jevge?ija,Turks, Māris
supporting information, p. 2727 - 2731 (2017/06/23)
Potassium allyltrifluoroborates underwent a bora-ene reaction with sulfur dioxide in the absence of Lewis acid catalysts to give sulfinyloxy-trifluoroborates, which subsequently undergo alkylation with electrophiles to produce sulfones in up to 91% yield. Benzyl halides and haloacetic acid derivatives can be used as the alkylation reagents while the Sanger reagent undergoes a SNAr reaction with sulfinyloxy-trifluoroborates to produce the corresponding 2,4-dinitrophenylsulfone. The developed method allows the transformation of potassium allyltrifluoroborates into allyl sulfones.
DABSO-based, three-component, one-pot sulfone synthesis
Deeming, Alex S.,Russell, Claire J.,Hennessy, Alan J.,Willis, Michael C.
supporting information, p. 150 - 153 (2014/01/23)
The addition of Grignard reagents or organolithium reagents to the SO 2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products. The metal sulfinates can be trapped in situ with a wide range of C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, and (hetero)aryliodoniums.
BCl3-mediated ene reaction of sulfur dioxide and-unfunctionalized alkenes
Markovic, Dean,Volla, Chandra M. R.,Vogel, Pierre,Varela-Alvarez, Adrian,Sordo, Jose A.
supporting information; experimental part, p. 5969 - 5975 (2010/09/04)
The first ene reactions of SO2 and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO 2 with alkenes can be used to generate β,γ-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of one equivalent of BCl3, the unstable sulfinic acid form stable sulfinic acid-BCl 3 complexes that can be reacted in situ with NCS to generate corresponding sulfonyl chlorides, or with a base to generate corresponding sulfinates. The latter can be reacted with electrophiles to generate sulfones, or with silyl chloride to form β,γ-unsaturated silyl sulfinates. The sulfinic acid-BCl3 complexes can be reacted with ethers that act as oxygen nucleophiles to produce corresponding sulfinic esters. Thus one-pot, three-component synthesis of β,γ-unsaturated sulfonamides, sulfinyl esters and sulfones have been developed starting from alkenes and sulfur dioxide (reagent and solvent).
The epoxy-Ramberg-Baecklund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols
Evans, Paul,Johnson, Paul,Taylor, Richard J. K.
, p. 1740 - 1754 (2007/10/03)
The epoxy-Ramberg-Baecklund reaction (ERBR) is outlined, in which α,β-epoxy sulfones are converted into a range of mono-, di- and tri-substituted allylic alcohols, on treatment with base. Modification of this method enabled the preparation of enantio-enriched allylic alcohols following the diastereoselective epoxidation of enantio-enriched vinyl sulfones that were accessed efficiently from the chiral pool. The scope, optimisation and limitations of the ERBR as a method for the preparation of allylic alcohols are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Simple, economical and environmentally friendly sulfone synthesis
Alonso, Diego A.,Nájera, Carmen,Varea, Montserrat
, p. 3459 - 3461 (2007/10/03)
Chemoselective sulfur oxidation of functionalized sulfides was developed using catalytic amounts of MnSO4·H2O (1 mol%) and 30% H2O2 in the presence of a buffer solution of NaHCO3. Aromatic and aliphatic sulfides were oxidized to sulfones in quantitative yields in 15 min. Different functional groups including double bonds, alcohols, ethers of THP and TBDMS groups were tolerated under these mild and green reaction conditions.
CYCLIZATION OF SELECTED BENZYL SULFONE DERIVATIVES UNDER PHASE TRANSFER CATALYTIC CONDITIONS
El-Zohry, Maher F.,El-Khawaga, Ahmed M.,Abdel-Wahab, Aboel-Magd A.
, p. 149 - 152 (2007/10/02)
Seven selected benzyl chloroalkyl sulfones (1a-c) and benzyl carboethoxyalkyl sulfones (1d-g) has been subjected to treatment with aqueous NaOH (50percent) under PTC conditions.Analysis of the product mixtures revealed competitive cyclization, elimination
Activation of Superoxide. Facile Oxidation of Sulfoxides into Sulfones with a Peroxysulfur Intermediate Generated in situ from 2-Nitrobenzenesulfonyl Chloride and Superoxide
KIM, Yong Hae,LEE, Hyeon Kyu
, p. 1499 - 1502 (2007/10/02)
Various sulfoxides, such as dialkyl, alkyl-aryl, and diaryl sulfoxides, were readily oxidized into the corresponding sulfones, in excellent yields under mild conditions, by 2-nitrobenzene peroxysulfur intermediate generated in situ from 2-nitrobenzene-sulfonyl chloride and potassium superoxide at -30 deg C, in dry acetonitrile.Chemoselective oxidation of sulfoxides which contain both double bond and sulfinyl moiety to the sulfones, was observed under the same conditions.
