Eosin-Mediated Alkylsulfonyl Cyanation of Olefins

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Pirenne V., Kurtay G., Voci S., Bouffier L., Sojic N., Robert F., ...More

Organic Letters, vol.20, no.15, pp.4521-4525, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 20 Issue: 15
  • Publication Date: 2018
  • Doi Number: 10.1021/acs.orglett.8b01828
  • Journal Name: Organic Letters
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4521-4525
  • Hacettepe University Affiliated: No


© 2018 American Chemical Society.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.