β-Selective Addition of Pyrroles to Electron-Deficient Alkenes in Both Catalytic and Stoichiometric Modes on B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>

To the best of our knowledge, the addition of pyrroles to electron-deficient alkenes (APEda) via electrophilic aromatic substitution (S<sub>E</sub>Ar) has been reported to occur exclusively at the α-position of the pyrrole without any formation, even in trace amounts, of a β-adduct, β-<b>3</b>. In sharp contrast to the prolonged immutable observation, we established an original S<sub>E</sub>Ar-based APEda (S<sub>E</sub>Ar-APEda) system applicable to both the catalytic and stoichiometric synthesis of β-<b>3</b>.

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Publication Details

Journal
ACS Omega
Published
2025-05-19
DOI
https://doi.org/10.1021/acsomega.5c00371
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

β-Selective Addition of Pyrroles to Electron-Deficient Alkenes in Both Catalytic and Stoichiometric Modes on B(C6F5)3

Takaaki Sonoda, Mitsuyasu Kawakami, Akira Ono, Teruhisa Tsuchimoto et al.
ACS Omega
Fluorine in Organic Chemistry
article

β-Selective Addition of Pyrroles to Electron-Deficient Alkenes in Both Catalytic and Stoichiometric Modes on B(C6F5)3

Takaaki Sonoda, Mitsuyasu Kawakami, Akira Ono, Teruhisa Tsuchimoto, Shinichi Sekine, Miho Kashiwa
article en

Abstract

To the best of our knowledge, the addition of pyrroles to electron-deficient alkenes (APEda) via electrophilic aromatic substitution (S<sub>E</sub>Ar) has been reported to occur exclusively at the α-position of the pyrrole without any formation, even in trace amounts, of a β-adduct, β-<b>3</b>. In sharp contrast to the prolonged immutable observation, we established an original S<sub>E</sub>Ar-based APEda (S<sub>E</sub>Ar-APEda) system applicable to both the catalytic and stoichiometric synthesis of β-<b>3</b>.

ACS OmegaVol. 10(21)
Meiji University (JP)
Meiji University
Openalex Percentile: Top 92%
Fluorine in Organic Chemistry
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β-Selective Addition of Pyrroles to Electron-Deficient Alkenes in Both Catalytic and Stoichiometric Modes on B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> — Takaaki Sonoda, Mitsuyasu Kawakami, et al. · ACS Omega (2025) | TGRS Research Map | TGRS