PIII/PV=O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles
PIII/PV=O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles
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DOI：
10.1002/anie.201914851
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发表时间：
2020-01-29
影响因子：
16.6
通讯作者：
Radosevich, Alexander T.
中科院分区：
文献类型：
--
作者：
Nykaza, Trevor, V;Li, Gen;Radosevich, Alexander T.
报道了一种模块化合成多种n -芳基和n -烷基氮杂环（吲哚、氧吲哚、苯并咪唑和喹草胺二酮）的有机催化方法。该方法采用小环有机磷基催化剂（1,2,2,3,4,4-六甲基磷烷对氧化物）和氢硅烷还原剂，通过与硼酸进行顺序的分子间还原C-N交叉偶联，然后进行分子内环化，驱动邻功能化硝基芳烃转化为氮杂环。该方法能够从现成的构建块快速构建氮杂环，包括对n取代苯并咪唑和喹草胺二酮的区域特异性方法。
An organocatalytic method for the modular synthesis of diverse N-aryl and N-alkyl azaheterocycles (indoles, oxindoles, benzimidazoles, and quinoxalinediones) is reported. The method employs a small-ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) and a hydrosilane reductant to drive the conversion of ortho-functionalized nitroarenes into azaheterocycles through sequential intermolecular reductive C-N cross coupling with boronic acids, followed by intramolecular cyclization. This method enables the rapid construction of azaheterocycles from readily available building blocks, including a regiospecific approach to N-substituted benzimidazoles and quinoxalinediones.