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

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

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...

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Veröffentlicht in:Journal of the American Chemical Society 2018-03, Vol.140 (11), p.3858-3862
Hauptverfasser: Toriumi, Naoyuki, Asano, Norihito, Miyamoto, Kazunori, Muranaka, Atsuya, Uchiyama, Masanobu
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container_end_page 3862
container_issue 11
container_start_page 3858
container_title Journal of the American Chemical Society
container_volume 140
creator Toriumi, Naoyuki
Asano, Norihito
Miyamoto, Kazunori
Muranaka, Atsuya
Uchiyama, Masanobu
description 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.
doi_str_mv 10.1021/jacs.8b00356
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title N‑Alkynylpyridinium Salts: Highly Electrophilic Alkyne–Pyridine Conjugates as Precursors of Cationic Nitrogen-Embedded Polycyclic Aromatic Hydrocarbons
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