P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles
Author(s)
Nykaza, Trevor V; Li, Gen; Yang, Junyu; Luzung, Michael R; Radosevich, Alexander T![Thumbnail](/bitstream/handle/1721.1/136626/nihms-1066025.pdf.jpg?sequence=4&isAllowed=y)
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© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
Date issued
2020Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Angewandte Chemie - International Edition
Publisher
Wiley