28995-78-0Relevant academic research and scientific papers
Iodine-catalyzed Sulfonylation of Arylacetylenic Acids and Arylacetylenes with Sodium Sulfinates: Synthesis of Arylacetylenic Sulfones
Meesin, Jatuporn,Katrun, Praewpan,Pareseecharoen, Chayaporn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Kuhakarn, Chutima
, p. 2744 - 2752 (2016/04/26)
A highly efficient and generally applicable iodine-catalyzed reaction of arylacetylenic acids and arylacetylenes with sodium sulfinates for the synthesis of arylacetylenic sulfones was developed. The methodology has the advantages of a metal-free strategy, easy to handle reagents, functional group tolerance, a wide range of arylacetylenic acids and arylacetylenes, and easy access to arylacetylenic sulfones. (Chemical Equation Presented).
Stereoselective silylcupration of conjugated alkynes in water at room temperature
Linstadt, Roscoe T. H.,Peterson, Carl A.,Lippincott, Daniel J.,Jette, Carina I.,Lipshutz, Bruce H.
supporting information, p. 4159 - 4163 (2014/05/06)
Micellar catalysis enables copper-catalyzed silylcupration of a variety of electron-deficient alkynes, thereby providing access to isomerically pure E- or Z-β-silyl-substituted carbonyl derivatives. These reactions take place in minutes, afford high yields and stereoselectivity, and are especially tolerant of functional groups present in the substrates. The aqueous reaction medium has been successfully recycled several times, and a substrate/catalyst ratio of 10,000:1 has been documented for this methodology. Fast, cheap, and green: Micellar catalysis enables the selective construction of a variety β-silyl-substituted carbonyl derivatives under mild aqueous conditions. The reaction is catalyzed by low levels of CuI, is compatible with numerous electron-withdrawing groups, affords high yields, and provides opportunities for scale-up and recycling of the reaction medium. The environmental impact, as measured by E Factors, is very low.
An improved synthesis of vinyl- and β-iodovinyl sulfones by a molecular iodine-mediated one-pot iodosulfonationdehydroiodination reaction
Sawangphon, Tassaporn,Katrun, Praewpan,Chaisiwamongkhol, Korbua,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
supporting information, p. 1692 - 1707 (2013/05/22)
An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective β-iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones
Katrun, Praewpan,Chiampanichayakul, Supanimit,Korworapan, Kanokwan,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Kuhakarn, Chutima
supporting information; experimental part, p. 5633 - 5641 (2010/12/25)
(Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yield
CAN mediated reaction of aryl sulfinates with alkenes and alkynes: Synthesis of vinyl sulfones, β-iodovinyl sulfones and acetylenic sulfones
Nair, Vijay,Augustine, Anu,Suja
, p. 2259 - 2265 (2007/10/03)
Cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate
Reactions of (E)-2-Iodo-1-tosyl-1-alkenes as Useful Synthetic Intermediates
Iwata, Noriyoshi,Morioka, Tetsuro,Kobayashi, Toshifumi,Asada, Takahiro,Kinoshita, Hideki,Inomata, Katsuhiko
, p. 1379 - 1388 (2007/10/02)
(E)-2-Iodo-1-tosyl-1-alkenes readily available by iodosulfonization of 1-alkynes were found to be useful synthons for the regio- and/or stereoselective preparation of 1-tosyl-1-alkynes, 1-tosyl-2-alkynes, (Z)-vinyl and (Z)-allyl sulfones, β-tosyl enamines
Regio- and Stereoselective Synthesis of (E)- and (Z)-Allylsulfones from Aldehydes and Alkynes
Ozawa, Motoyasu,Iwata, Noriyoshi,Kinoshita, Hideki,Inomata, Katsuhiko
, p. 1689 - 1692 (2007/10/02)
Several (E)- and (Z)-1-p-toluenesulfonyl(=tosyl)-2-alkenes, allylsulfones, were regio- and stereoselectively prepared from aldehydes and alkynes, respectively, in good yields by application of the results of our previous investigation on "syn-effect" and
Regio- and Stereoselective Synthesis of (E)- and (Z)-Vinylic Sulfones and Their Conversion to the Corresponding Allylic Sulfones
Kobayashi, Toshifumi,Tanaka, Yuhji,Ohtani, Takashi,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
, p. 1209 - 1212 (2007/10/02)
(E)- and (Z)-vinilyc sulfones were prepared regio- and stereoselectively from 1-alkenes or 1-alkynes in high yields via iodosulfonization in AcOEt-H2O.The vinylic sulfones thus prepared were converted to the corresponding allylic sulfones by treatment wit
Organic synthesis with sulfones no. XXXV. Iron catalysed condensation and hydrogenolysis of vinylic sulfones with Grignard reagents. A stereoselective synthesis of di- and trisubstituted olefins
Fabre, Jean-Luc,Julia, Marc,Verpeaux, Jean-Noel
, p. 772 - 778 (2007/10/02)
Vinylic sulfones are readily available in the E or Z configuration.Condensation with primary Grignard reagents occurs stereospecifically in the presence of iron catalysts, leading to trisubstituted olefins.With secondary Grignards stereospecific hydrogenolysis to 1,2-disubstituted olefins is observed.
