24225-08-9Relevant academic research and scientific papers
P-Anisaldehyde-Photosensitized Sulfonylcyanation of Chiral Cyclobutenes: Enantioselective Access to Cyclic and Acyclic Systems Bearing All-Carbon Quaternary Stereocenters
Pirenne, Vincent,Traboulsi, Iman,Rouvière, Lisa,Lusseau, Jonathan,Massip, Stéphane,Bassani, Dario M.,Robert, Frédéric,Landais, Yannick
supporting information, p. 575 - 579 (2020/01/09)
The photosensitized p-Anisaldehyde-mediated addition of sulfonylcyanides onto the I -system of cyclobutenes is shown to afford highly functionalized cyclobutanes in high yields and diastereocontrol. The homochiral cyclobutene precursors are accessible on multigram scale in two steps through an asymmetric [2 + 2] cycloaddition/vinyl thioether reduction sequence. The enantiopure cyclobutylnitriles can be elaborated further through SmI2-mediated ring opening or converted into new enantiopure cyclobutenes through base-mediated sulfone elimination.
Eosin-Mediated Alkylsulfonyl Cyanation of Olefins
Pirenne, Vincent,Kurtay, Gülbin,Voci, Silvia,Bouffier, Laurent,Sojic, Neso,Robert, Frédéric,Bassani, Dario M.,Landais, Yannick
supporting information, p. 4521 - 4525 (2018/08/09)
Eosin-Y (EY)-mediated alkylsulfonyl cyanation of olefins was shown to afford alkylsulfonyl nitriles in good yields. On the basis of transient absorption spectroscopy, the reaction was shown to proceed via photoinduced electron transfer from 3EY? to an O-cyanated derivative of the photocatalyst, formed in situ, with generation of the corresponding sulfinate that is oxidized by EY?.+ into a sulfonyl radical. Addition of the latter on the olefin, followed by a radical cyano group transfer, then furnished the nitrile along with a RSO2 radical sustaining the radical chain.
