Work

PIII/PV=O Catalyzed Cascade Synthesis of N‐Functionalized Azaheterocycles

Year: 2019

Type: article

Abstract: 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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201914851

Authors: Trevor V. Nykaza, Gen Li, Junyu Yang, Michael R. Luzung, Alexander T. Radosevich

Institutions: Massachusetts Institute of Technology, Kallyope (United States)

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G8000762917, Synthetic Methods based on Biphilic Phosphorus Catalysts