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A predictive model for additions to N-alkyl pyridiniums

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Abstract

Disclosed in this communication is a thorough study on the dearomative addition of organomagnesium nucleophiles to N-alkyl pyridinium electrophiles. The regiochemical outcomes have observable and predictable trends associated with the substituent patterns on the pyridinium electrophile. Often, the substituent effects can be either additive, giving high selectivities, or ablative, giving competing outcomes. Additionally, the nature of the organometallic nucleophilic component was also investigated for its role in the regioselective outcome. The effects of either reactive component are important to both the overall reactivity and site of nucleophilic addition. The utility of these observed trends is demonstrated in a concise, dearomative synthesis of a tricyclic compound shown to have insecticidal activity.

Graphical abstract: A predictive model for additions to N-alkyl pyridiniums

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Article information


Submitted
05 Jan 2021
Accepted
08 Jan 2021
First published
11 Jan 2021

Chem. Commun., 2021, Advance Article
Article type
Communication

A predictive model for additions to N-alkyl pyridiniums

B. J. Knight, Z. A. Tolchin and J. M. Smith, Chem. Commun., 2021, Advance Article , DOI: 10.1039/D1CC00056J

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