Graduate School of Pharmaceutical Sciences, Kyoto University , Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Org Lett. 2017 Jun 16;19(12):3327-3330. doi: 10.1021/acs.orglett.7b01538. Epub 2017 Jun 7.
An unprecedented KHMDS-promoted domino reaction to furnish hydroxyfluoranthenes is described. Biaryl compounds bearing acyl and naphthylalkenyl moieties are transformed into 9-hydroxydibenzo[j,l]fluoranthenes in a single step through the formation of an aromatic and a pentagonal ring system. A variety of fluoranthenes including those with extended π-conjugation, a heteroaromatic ring, and unsymmetrical substituents could be synthesized. Mechanistic studies reveal a unique reaction cascade where KHMDS acts as both a base and a single-electron donor.
描述了一种前所未有的 KHMDS 促进的多米诺反应，以提供羟基荧蒽。通过形成一个芳香环和一个五员环体系，带有酰基和萘基烯基部分的联苯化合物在一步中转化为 9-羟基二苯并[j,l]荧蒽。可以合成各种荧蒽，包括具有扩展的π共轭、杂芳环和不对称取代基的荧蒽。机理研究揭示了一种独特的反应级联，其中 KHMDS 既作为碱又作为单电子供体。
