Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior S. N., Ciudad Universitaria, Coyoacán, Ciudad de México 04510, Mexico.
Org Biomol Chem. 2020 May 13;18(18):3487-3491. doi: 10.1039/d0ob00136h.
A photocatalytic xanthate-based radical addition/cyclization reaction cascade toward 2-biphenylisocyanides is described as a practical and modular approach to 6-alkylated phenanthridines. The use of xanthates as radical precursors allowed the synthesis of diversely 6-substituted phenanthridines. Electrophilic radicals derived from nitriles, aromatic and aliphatic ketones, malonates, and amide derivatives, as well as radicals derived from phthalimidomethyl and benzylic derivatives were successfully introduced. The reaction proceeds under mild conditions without a stoichiometric amount of oxidant. Thirty novel phenanthridine scaffolds were synthesized with yields ranging from 24 to 76%.
描述了一种光催化黄原酸酯基自由基加成/环化反应级联反应，用于制备 2-联苯异氰化物，这是一种实用且模块化的方法，可以制备各种 6-烷基化的菲啶。黄原酸酯作为自由基前体的使用允许合成不同的 6-取代的菲啶。成功引入了来自腈、芳香族和脂肪族酮、丙二酸酯和酰胺衍生物的亲电自由基，以及来自邻苯二甲酰亚甲基和苄基衍生物的自由基。反应在温和条件下进行，无需氧化剂的化学计量。通过该反应合成了 30 种新型菲啶支架，产率范围为 24%至 76%。
