Co(III)-Catalyzed Three-Component Cascade for the Synthesis of α-Quaternary Acyclic Nitriles <i>via</i> C–H Bond Activation

Herein, we developed a cobalt-catalyzed three-component strategy to synthesize α-quaternary aliphatic nitriles in good yields. This protocol proceeds through the sequential addition of indoles, dienes, and <i>N</i>-cyanosuccinimide. The scope of this method has been extensively explored with various substituted <i>N</i>-pyrimidyl-indoles. Terminally substituted diene and 1,2-disubstituted diene also participated in the reaction. Notably, <i>N</i>-pyridyl-2-pyridones are also compatible with this protocol. The synthesized nitrile product was further converted into a tetrazole derivative. A plausible reaction mechanism is proposed to account for the present transformation.

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Publication Details

Journal
Organic Letters
Published
2025-12-11
DOI
https://doi.org/10.1021/acs.orglett.5c04508
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Co(III)-Catalyzed Three-Component Cascade for the Synthesis of α-Quaternary Acyclic Nitriles via C–H Bond Activation

Masilamani Jeganmohan, Priyambada Prusty
Organic Letters
Catalytic C–H Functionalization Methods
article

Co(III)-Catalyzed Three-Component Cascade for the Synthesis of α-Quaternary Acyclic Nitriles via C–H Bond Activation

Masilamani Jeganmohan, Priyambada Prusty
article en

Abstract

Herein, we developed a cobalt-catalyzed three-component strategy to synthesize α-quaternary aliphatic nitriles in good yields. This protocol proceeds through the sequential addition of indoles, dienes, and <i>N</i>-cyanosuccinimide. The scope of this method has been extensively explored with various substituted <i>N</i>-pyrimidyl-indoles. Terminally substituted diene and 1,2-disubstituted diene also participated in the reaction. Notably, <i>N</i>-pyridyl-2-pyridones are also compatible with this protocol. The synthesized nitrile product was further converted into a tetrazole derivative. A plausible reaction mechanism is proposed to account for the present transformation.

Organic LettersVol. 27(51)
Indian Institute of Technology Madras (IN)
Openalex Percentile: Top 70%
Catalytic C–H Functionalization Methods
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