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

**Authors:** Seina Sekine, Miho Kashiwa, Maho Kawakami, Takumi Sonoda, Arisa Ono, Teruhisa Tsuchimoto

PMC · DOI: 10.1021/acsomega.5c00371 · ACS Omega · 2025-05-19

## TL;DR

This paper reports a new method for adding pyrroles to electron-deficient alkenes at the beta position using B(C6F5)3.

## Contribution

The study introduces a novel electrophilic aromatic substitution system for beta-selective addition of pyrroles.

## Key findings

- A beta-adduct was successfully formed using B(C6F5)3 in both catalytic and stoichiometric modes.
- The reaction system enables selective addition at the beta-position of pyrroles.
- This contrasts with previous reports that only alpha-adducts were formed.

## Abstract

To the best of our knowledge, the addition of pyrroles
to electron-deficient
alkenes (APEda) via electrophilic aromatic substitution (SEAr) 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-3. In sharp contrast to the prolonged
immutable observation, we established an original SEAr-based
APEda (SEAr-APEda) system applicable to both the catalytic
and stoichiometric synthesis of β-3.

## Linked entities

- **Chemicals:** B(C6F5)3 (PubChem CID 582056)

## Full-text entities

- **Chemicals:** Pyrroles (MESH:D011758), Alkenes (MESH:D000475), S (MESH:D013455), Ar (MESH:D001128), E (MESH:D004540), APEda (-)

## Full text

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## Figures

14 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12138597/full.md

## References

24 references — full list in the complete paper: https://tomesphere.com/paper/PMC12138597/full.md

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Source: https://tomesphere.com/paper/PMC12138597