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A Predictive Model for Additions to N-Alkyl Pyridiniums

preprint
submitted on 22.10.2020, 19:47 and posted on 23.10.2020, 15:06 by Brian Knight, Zachary Tolchin, Joel Smith
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.

History

Email Address of Submitting Author

smith@chem.fsu.edu

Institution

Florida State University

Country

United States

ORCID For Submitting Author

0000-0002-1108-4751

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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