73082-82-3Relevant academic research and scientific papers
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.
α-Sulfonyl succinimides: Versatile sulfinate donors in Fe-catalyzed, salt-free, neutral allylic substitution
Jegelka, Markus,Plietker, Bernd
, p. 10417 - 10430 (2011/10/31)
Allyl sulfones are versatile intermediates in organic chemistry. The presence of two distinct functional groups sets the stage for a plethora of subsequent transformations. However, despite these advantages the preparation of regioisomerically enriched sulfones is not easy. The use of sulfinate salts as nucleophiles in substitutions is frequently accompanied by side reactions such as π-bond migration, β-elimination, and so on. Herein we present a preparatively simple way to synthesize a variety of different aryl or alkyl allyl sulfones starting from readily accessible allylic carbonates. By employing aryl or alkyl α-sulfonyl succinimides as sulfinate synthons, mild and regioselective ipso substitution of diverse allylic carbonates was realized.
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).
