Doobary Sayad, Poole Darren L, Lennox Alastair J J
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
Medicines Design, GSK Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, U.K.
J Org Chem. 2021 Nov 19;86(22):16095-16103. doi: 10.1021/acs.joc.1c01946. Epub 2021 Nov 12.
The 3-substituted chromane core is found in several bioactive natural products. Herein, we describe a route to 3-fluorinated chromanes from allylic phenol ethers. Our external oxidant-free approach takes advantage of an electrochemical generation of a hypervalent iodine species, difluoro-λ-tolyl iodane, which mediates the alkene fluoroarylation. High yields and selectivity for this transformation are achieved for electron poor substrates. The redox chemistry has been characterized for the electrochemical generation of the iodane in the presence of fluoride, and insights into the mechanism are given. The transformation has been demonstrated on gram scales, which indicates the potential broader utility of the process.
3-取代色满核心存在于多种生物活性天然产物中。在此，我们描述了一种从烯丙基酚醚制备3-氟色满的方法。我们的无外部氧化剂方法利用电化学产生的高价碘物种二氟-λ-甲苯碘烷，其介导烯烃氟芳基化反应。对于贫电子底物，该转化反应具有高收率和选择性。已对在氟化物存在下电化学产生碘烷的氧化还原化学进行了表征，并给出了反应机理的见解。该转化反应已在克级规模上得到证明，这表明该方法具有更广泛的潜在应用价值。
