Sumter Kelsey T, Slough Carly, Johnson Hayley E, Kesler Catherine S, Daub Mary Elisabeth
Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States.
J Org Chem. 2025 Sep 26;90(38):13488-13495. doi: 10.1021/acs.joc.5c01187. Epub 2025 Sep 11.
β-Distabilized iodonium ylides undergo photocatalytic activation using neutral eosin Y and visible light to afford dihydrofuropyranones, dihydrofuropyridones, and dihydrofurans. Steady-state absorption spectroscopy and application of the method of continuous variations to complexation-induced chemical shifts provide evidence for the binary complexation of eosin Y and β-distabilized iodonium ylides. Preliminary mechanistic studies using transient absorption spectroscopy suggest monoanionic eosin Y as the active photocatalyst functioning via an oxidative quenching cycle. This simple approach to enhancing the reactivity of heterocyclic iodonium ylides expands the scope of their use as building blocks in the synthesis of heterocycles.
β-不稳定碘鎓叶立德在中性曙红Y和可见光的作用下进行光催化活化，生成二氢呋喃并吡喃酮、二氢呋喃并吡啶酮和二氢呋喃。稳态吸收光谱以及连续变化法在络合诱导化学位移中的应用为曙红Y与β-不稳定碘鎓叶立德的二元络合提供了证据。使用瞬态吸收光谱进行的初步机理研究表明，单阴离子曙红Y作为活性光催化剂，通过氧化猝灭循环发挥作用。这种提高杂环碘鎓叶立德反应活性的简单方法扩展了它们作为杂环合成砌块的应用范围。
