P III /P V =O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles
Name
nihms-1066025.pdf
Description
Accepted version
Size
1.27 MB
Format
Adobe PDF
Checksum (MD5)
377f4978f2d2076cf1ac1052157efac9
Author(s)
Nykaza, Trevor V
Li, Gen
Yang, Junyu
Luzung, Michael R
Radosevich, Alexander T
Date Issued
2020
Journal
Angewandte Chemie - International Edition
Publisher
Wiley
Version
Author's final manuscript
Abstract
© 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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1002/ANIE.201914851
