52920-44-2Relevant academic research and scientific papers
Aerobic copper-catalyzed synthesis of (E)-alkenyl sulfones and (E)-β-halo-alkenyl sulfones via addition of sodium sulfinates to alkynes
Taniguchi, Nobukazu
supporting information, p. 1984 - 1990 (2014/03/21)
Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the reaction using CuI catalyst produced (E)-β-haloalkenyl sulfones anti-selectively in the presence of potassium halides. Furthermore, the (E)-β-bromoalkenyl sulfones are possible to convert into various alkenyl sulfones by Suzuki-Miyaura coupling.
Convenient ambient temperature generation of sulfonyl radicals
Gilmore, Kerry,Gold, Brian,Clark, Ronald J.,Alabugin, Igor V.
, p. 336 - 340 (2013/05/08)
Presented herein is a novel method for the efficient, ambient temperature generation of sulfonyl radicals from aryl and alkyl sulfonylbromides upon autoxidation of triethylborane (Et3B). The resultant radicals were regioselectively trapped via addition to terminal alkynes, generating a secondary vinyl radical that selectively abstracts a Br atom from RSO 2Br, yielding the (E)-bromo vinylsulfones. Sensitivity towards Lewis basic groups was observed, presumably due to the disruptive coordination to Et3B before atom-transfer.
Stereoselective synthesis of (E)-alkenyl sulfones from alkenes or alkynes via copper-catalyzed oxidation of sodium sulfinates
Taniguchi, Nobukazu
supporting information; experimental part, p. 1308 - 1312 (2011/07/07)
Alkenyl sulfones can be stereoselectively synthesized from alkenes or alkynes using sodium sulfinates. The reaction can be performed by a copper-catalyzed oxidation of sodium sulfinates in air. The reaction of alkenes gives (E)-alkenyl sulfones via anti addition of sulfonyl cation and elimination process. Furthermore, the employment of alkynes produces (E) β- haloalkenyl sulfones in the presence of potassium halides. Georg Thieme Verlag Stuttgart · New York.
Condensation products of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates
Vasin,Bolusheva,Razin
experimental part, p. 419 - 429 (2009/04/11)
Bromomethyl (E)-2-phenylethenyl and bromomethyl (Z)-1-bromo-2-phenylethenyl sulfones undergo condensation with enolates generated from malononitrile, dimethyl malonate, methyl and ethyl acetoacetate using NaH in THF to give tetrahydrothiophene S,S-dioxide
