Pyridinium Design for Deaminative Reactions of Sterically Encumbered Alkyl Amines

Organic Letters 2026 Open access

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Authors: Obieze C. Enudi, J. Cameron Twitty, Madeline E. Rotella, Steven J. Underwood, Marisa C. Kozlowski, Mary P. Watson
DOI: 10.1021/acs.orglett.6c01717
Cited by: 1
References: 36

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.

Fields of Study & Subjects

Catalytic C–H Functionalization Methods Catalytic Cross-Coupling Reactions Asymmetric Hydrogenation and Catalysis

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
22
Pages
7009–7014
Publication date
24 May 2026
Language
EN