Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment,Angewandte Chemie International Edition

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Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2023-06-09 , DOI: 10.1002/anie.202305081
Ben W Joynson ₁ , Graham R Cumming ₂ , Liam T Ball ₁

Affiliation

We demonstrate that pyridinium and quinolinium salts can be accessed by the insertion of a single C-atom from an arylchlorodiazirine into the parent N-alkyl pyrrole or indole. The azinium products of ring expansion are activated towards oxygenation and hydrogenation, expediting further structural diversification. Safer methods for the use of diazirines as carbene precursors have been developed with insight from differential scanning calorimetry.

中文翻译：

光化学介导的吲哚和吡咯与氯二嗪的扩环：合成方法和热危害评估

我们证明，吡啶盐和喹啉盐可以通过将芳基氯二氮丙啶的单个C原子插入母体N-烷基吡咯或吲哚来获得。扩环的吖嗪产物被激活用于氧化和氢化，加速结构的进一步多样化。根据差示扫描量热法的见解，已经开发出使用二氮丙啶作为卡宾前体的更安全的方法。

更新日期：2023-06-09

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