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DOI: 10.1055/s-0043-1775450
Nucleophilic Addition to N-Vinylpyridiniums by Using Ion-Pair Extraction with Tetracyanocyclopentadienides
This research was partially supported by Grant-in-Aids for Scientific Research (C) (22K06539) from the Japan Society for the Promotion of Science (JSPS), research fund from the Research Institute of Meijo University, and the Meijo University Research Promotion Organization for Carbon Neutrality.
Abstract
N-Vinylpyridinium is a useful electrophilic species in synthetic organic chemistry. In this study, we reinvestigated the addition reaction of N-vinylpyridinium, which has received limited attention in the past several decades. The reaction conditions were screened in detail with the aid of tetracyanocyclopentadienide (TCCP) ion-pair extraction and its extraction prediction equation, and the optimal reaction conditions were identified to entail the use of 2,2,2-trifluoroethanol (TFE) as an additive and dichloromethane as solvent. We successfully obtained 14 addition products with various substitution patterns, among which 3,5-dimethyl-N-vinylpyridinium provided the addition product in up to 85% yield. The reduction of the pyridinium core advanced smoothly, indicating that the TCCP anions did not significantly influence the reactivity of the platinum-catalyzed hydrogenation.
Key words
ion-pair extraction - addition - pyridinium - tetracyanocyclopentadienide - nitrogen heterocycleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775450.
- Supporting Information
Publication History
Received: 14 December 2024
Accepted after revision: 27 January 2025
Article published online:
04 March 2025
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