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Updated: May 25, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Pyridinium Design for Deaminative Reactions of Sterically Encumbered Alkyl Amines
Obieze C Enudi1, J Cameron Twitty1, Madeline E Rotella2
1Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Abstract:
We introduce a new 3,5-diphenylpyridinium motif that can be readily installed on α-tertiary alkyl amines and enables effective deamination. This advance overcomes the limitation that Katritzky pyridinium salts cannot be accessed from α-tertiary alkyl amines. Use of this 3,5-diphenylpyridinium salt enables a nickel-catalyzed reductive alkylation of Michael acceptors to construct quaternary carbons with a broad range of tertiary alkyl groups. Density functional theory (DFT) calculations were used to understand the surprising reactivity difference between adamantyl and other tertiary alkyl groups.
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