Chapter one provides an overview of phosphine oxide catalysis, encompassing two strategies: redox-neutral and redox-driven phosphine oxide catalysis. It highlights some of the important examples reported in the literature, providing essential context for the subsequent chapter. Chapter two explores the development of innovative bridged [2.1.1] bicyclic phosphine oxides. These compounds are synthesized through a concise five-step process using readily available starting materials. Notably, we investigate silane-mediated reductions of bridged [2.1.1] bicyclic phosphine oxides and other known phosphine oxides, employing 31P NMR spectroscopy to assess their performances. Our findings reveal the superiority of these novel phosphine oxides over their current best-in-class counterparts, as they demonstrate a notably faster reduction rate at room temperature. Moreover, we showcase the practical application of these novel phosphine oxides in peptide coupling, offering a valuable complement to existing peptide synthesis methods. Chapter three delves into the realm of dealkenylative alkenylation. The dealkenylative alkenylation of alkene C(sp3)−C(sp2) bonds represents an underexplored avenue for C−C bond formation. The β-alkylated styrene derivatives (up to 64 examples) are synthesized by reacting easily accessible feedstock olefins with β-nitrostyrenes through ozone/FeII-mediated radical coupling, with high yield and good stereoselectivity. All the reactions are conducted under mild conditions, showcasing an impressive tolerance for a wide range of functional groups. Furthermore, we extend the utility of this methodology by demonstrating its efficacy in the synthesis of two significant compounds: the natural product iso-moracin and the pharmaceutical compound (E)-metanicotine.
Cookie SettingseScholarship uses cookies to ensure you have the best experience on our website. You can manage which cookies you want us to use.Our Privacy Statement includes more details on the cookies we use and how we protect your privacy.