Intramolecular cyclization of m-homoprenylphenols through oxidative nucleophilic aromatic substitution

Hiroki Deguchi; Kengo Hanaya; Takeshi Sugai; Shuhei Higashibayashi

doi:10.1039/d2cc06026d

Intramolecular cyclization of m-homoprenylphenols through oxidative nucleophilic aromatic substitution

Hiroki Deguchi, Kengo Hanaya, Takeshi Sugai, Shuhei Higashibayashi

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

We developed an intramolecular cyclization of m-homoprenylphenols and related m-prenylphenols to bicyclic skeletons by hypervalent iodine reagents through an oxidative nucleophilic aromatic substitution using the prenyl group as a carbon nucleophile. The reaction was applicable for the syntheses of 5/6-, 6/6-, and 7/6-fused ring systems.

Original language	English
Pages (from-to)	748-751
Number of pages	4
Journal	Chemical Communications
Volume	59
Issue number	6
DOIs	https://doi.org/10.1039/d2cc06026d
Publication status	Published - 2022 Dec 15

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d2cc06026d

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abstract = "We developed an intramolecular cyclization of m-homoprenylphenols and related m-prenylphenols to bicyclic skeletons by hypervalent iodine reagents through an oxidative nucleophilic aromatic substitution using the prenyl group as a carbon nucleophile. The reaction was applicable for the syntheses of 5/6-, 6/6-, and 7/6-fused ring systems.",

author = "Hiroki Deguchi and Kengo Hanaya and Takeshi Sugai and Shuhei Higashibayashi",

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AU - Deguchi, Hiroki

AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Higashibayashi, Shuhei

PY - 2022/12/15

Y1 - 2022/12/15

N2 - We developed an intramolecular cyclization of m-homoprenylphenols and related m-prenylphenols to bicyclic skeletons by hypervalent iodine reagents through an oxidative nucleophilic aromatic substitution using the prenyl group as a carbon nucleophile. The reaction was applicable for the syntheses of 5/6-, 6/6-, and 7/6-fused ring systems.

AB - We developed an intramolecular cyclization of m-homoprenylphenols and related m-prenylphenols to bicyclic skeletons by hypervalent iodine reagents through an oxidative nucleophilic aromatic substitution using the prenyl group as a carbon nucleophile. The reaction was applicable for the syntheses of 5/6-, 6/6-, and 7/6-fused ring systems.

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Intramolecular cyclization of m-homoprenylphenols through oxidative nucleophilic aromatic substitution

Abstract

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