University of Bordeaux, Institute of Molecular Sciences , UMR-CNRS 5255, 351 cours de la Libération , 33405 Talence , France.
Org Lett. 2018 Aug 3;20(15):4521-4525. doi: 10.1021/acs.orglett.8b01828. Epub 2018 Jul 26.
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 EY* 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 RSO radical sustaining the radical chain.
曙红 Y（EY）介导的烯烃的烷基亚磺酰基氰化反应以良好的收率得到烷基亚磺酰基腈。基于瞬态吸收光谱，该反应通过 EY*向光催化剂的原位形成的 O-氰化衍生物的光诱导电子转移进行，生成相应的亚磺酸盐，后者被 EY 氧化成亚磺酰基自由基。后者加成到烯烃上，然后进行自由基氰基基团转移，得到腈以及维持自由基链的 RSO 自由基。
