Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

Installation of an alkyl chain at a specified position in the aromatic ring via metal-free catalysis is very important. In this regard, we have developed a facile metal-free, extremely selective, user-friendly, environmentally benign and costeffective Friedel-Crafts (FC) alkylation protocol for 2-oxindoles and anilines with donor-acceptor cyclopropanes. Real-time NMR studies reveal that the transformation is governed by the cooperative catalysis of Brønsted acid (TfOH) and HFIP, which facilitates the nucleophilic attack on donor-acceptor cyclopropanes from 2-oxindoles and anilines.

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HFIP & Brønsted Acid Promoted Direct Distal C‐Alkylation of 2‐Oxindoles and Anilines with Donor‐Acceptor Cyclopropanes

Singh

Lamba

Singh

et al. 2023

Adv Synth Catal

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Imidazol-5-one-based donor–acceptor cyclopropanes in reaction with C=S dipolarophiles

Nikolaev

Соколов

Mikhaylov

et al. 2022

Chem Heterocycl Comp

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Recent advances in ring-opening reactions of 2-substituted donor-acceptor cyclopropanes under metal catalysis

Doraghi,

Karimian,

Qareaghaj

et al. 2024

Journal of Organometallic Chemistry

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Nucleophilic ring opening of imidazolone activated donor–acceptor cyclopropanes with alcohols

Cited by 5 publications

References 22 publications

HFIP & Brønsted Acid Promoted Direct Distal C‐Alkylation of 2‐Oxindoles and Anilines with Donor‐Acceptor Cyclopropanes

HFIP & Brønsted Acid Promoted Direct Distal C‐Alkylation of 2‐Oxindoles and Anilines with Donor‐Acceptor Cyclopropanes

Imidazol-5-one-based donor–acceptor cyclopropanes in reaction with C=S dipolarophiles

Recent advances in ring-opening reactions of 2-substituted donor-acceptor cyclopropanes under metal catalysis

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