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PIII /PV =O Catalyzed Cascade Synthesis of N-Functionalized Azaheterocycles.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-29 , DOI: 10.1002/anie.201914851 Trevor V Nykaza 1 , Gen Li 1 , Junyu Yang 1 , Michael R Luzung 2 , Alexander T Radosevich 1
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-01-29 , DOI: 10.1002/anie.201914851 Trevor V Nykaza 1 , Gen Li 1 , Junyu Yang 1 , Michael R Luzung 2 , Alexander T Radosevich 1
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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.
中文翻译：
PIII / PV = O催化N-官能化氮杂环杂环化合物的级联合成。
报道了一种有机催化方法，用于模块化合成各种N-芳基和N-烷基氮杂杂环（吲哚，羟吲哚，苯并咪唑和喹喔啉二酮）。该方法采用小环有机磷基催化剂（1,2,2,3,4,4-六甲基膦烷P-氧化物）和氢化硅烷还原剂通过顺序的分子间还原性CN交联来驱动邻官能化硝基芳烃转化成氮杂杂环与硼酸偶联，然后进行分子内环化。该方法能够从容易获得的结构单元快速构建氮杂杂环，包括针对N取代的苯并咪唑和喹喔啉二酮的区域特异性方法。
更新日期：2020-01-29
中文翻译：
PIII / PV = O催化N-官能化氮杂环杂环化合物的级联合成。
报道了一种有机催化方法，用于模块化合成各种N-芳基和N-烷基氮杂杂环（吲哚，羟吲哚，苯并咪唑和喹喔啉二酮）。该方法采用小环有机磷基催化剂（1,2,2,3,4,4-六甲基膦烷P-氧化物）和氢化硅烷还原剂通过顺序的分子间还原性CN交联来驱动邻官能化硝基芳烃转化成氮杂杂环与硼酸偶联，然后进行分子内环化。该方法能够从容易获得的结构单元快速构建氮杂杂环，包括针对N取代的苯并咪唑和喹喔啉二酮的区域特异性方法。
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