Iodine‐mediated intramolecular coupling of C−H and N−H bonds through radical pathways has been achieved for the synthesis of substituted phenanthridinones from 2‐phenylbenzamides using iodine, succininmide and di‐tert‐butylperoxide (DTBP) oxidant in dichloroethane at 130 °C. The developed protocol provides substituted phenanthridinones, particularly N‐alkyl substituted, which are difficult to access either by base‐mediated or transition‐metal‐catalyzed methodologies due to acidic nature of the C−H bond adjacent to nitrogen atom in the amides. Serendipitously, switching the oxidant from DTBP to phenyliodine(III) diacetate (PIDA) afforded spiro‐isoindolinones, involving intramolecular C−N, intermolecular C−O coupling and dearomatization of the phenyl ring in one pot.

中文翻译：

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N-取代的菲啶酮和螺-异吲哚满酮的无过渡金属合成：C（sp2）-N和C（sp2）-O通过自由基途径偶联

在130°C的二氯乙烷中，使用碘，琥珀酰亚胺和二叔丁基过氧化物（DTBP）氧化剂，通过自由基途径实现了碘介导的CH和NH键分子内偶联，从2-苯基苯甲酰胺合成取代的菲啶酮。 。发达的协议提供了取代的菲啶酮类化合物，尤其是被N-烷基取代的菲，由于酰胺中与氮原子相邻的CH键的酸性，很难通过碱介导的或过渡金属催化的方法来获得。偶然地，将氧化剂从DTBP转换为二乙酸苯基碘（III）（PIDA），得到了螺-异吲哚满酮，涉及分子内CN，分子间C-O偶联和一锅中苯环的脱芳香化作用。