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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.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914851
Subject(s) - intramolecular force , chemistry , catalysis , combinatorial chemistry , medicinal chemistry , ring (chemistry) , halogenation , organic chemistry
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.