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N-Alkynylpyridinium Salts: Highly Electrophilic Alkyne–Pyridine Conjugates as Precursors of Cationic Nitrogen-Embedded Polycyclic Aromatic Hydrocarbons

Author:
Toriumi, Naoyuki, Asano, Norihito, Miyamoto, Kazunori, Muranaka, Atsuya, Uchiyama, Masanobu
Source:
Journal of the American Chemical Society 2018 v.140 no.11 pp. 3858-3862
ISSN:
1520-5126
Subject:
Lewis acids, cycloaddition reactions, electrochemistry, moieties, polycyclic aromatic hydrocarbons, pyridines, salts
Abstract:
We achieved the first synthesis of N-alkynylpyridinium salts, by reacting pyridines with alkynyl-λ³-iodanes. The N-alkynylpyridiniums exhibit highly electron-accepting character with extended π-conjugation. The electrophilic alkynyl groups were readily susceptible to Michael addition and 1,3-dipolar cycloaddition to afford various N-alkenylpyridiniums. Ring-fused pyridiniums were synthesized through intramolecular cyclization, demonstrating the utility of N-alkynylpyridiniums for the design of various electron-deficient cationic nitrogen-embedded polycyclic aromatic hydrocarbons with unique optical and electrochemical properties.
Agid:
6033118