Asymmetric Aerobic Intramolecular Dearomative <i>ortho</i> Coupling of Tethered Phenols by Chromium-Salen Complex/Nitroxyl Radical Catalysis

Herein, we report the catalytic asymmetric intramolecular dearomative coupling of tethered phenols in ortho-para fashion under aerobic conditions. Cooperative catalysis with a chromium-salen complex/nitroxyl radical enabled the desired transformation to proceed at ambient temperature under oxygen atmosphere. A range of tethered phenols were efficiently converted into spirocyclic 2,4-dienones in moderate to good yields and enantioselectivities (up to 68% enantiomeric excess (ee)).

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Journal
Chemical and Pharmaceutical Bulletin
Published
2026-01-29
DOI
https://doi.org/10.1248/cpb.c25-00762
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Asymmetric Aerobic Intramolecular Dearomative ortho Coupling of Tethered Phenols by Chromium-Salen Complex/Nitroxyl Radical Catalysis

Yusuke Sasano, Shogo Fujiki, Y. Iwabuchi, Nao Yokota et al.
Chemical and Pharmaceutical Bulletin
Catalytic C–H Functionalization Methods
article

Asymmetric Aerobic Intramolecular Dearomative ortho Coupling of Tethered Phenols by Chromium-Salen Complex/Nitroxyl Radical Catalysis

Yusuke Sasano, Shogo Fujiki, Y. Iwabuchi, Nao Yokota, Shota Nagasawa
article en

Abstract

Herein, we report the catalytic asymmetric intramolecular dearomative coupling of tethered phenols in ortho-para fashion under aerobic conditions. Cooperative catalysis with a chromium-salen complex/nitroxyl radical enabled the desired transformation to proceed at ambient temperature under oxygen atmosphere. A range of tethered phenols were efficiently converted into spirocyclic 2,4-dienones in moderate to good yields and enantioselectivities (up to 68% enantiomeric excess (ee)).

Chemical and Pharmaceutical BulletinVol. 74(1)
Tohoku University (JP)
Japan Agency for Medical Research and Development, Shorai Foundation for Science and Technology, Japan Society for the Promotion of Science
Openalex Percentile: Top 73%
Catalytic C–H Functionalization Methods
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Asymmetric Aerobic Intramolecular Dearomative <i>ortho</i> Coupling of Tethered Phenols by Chromium-Salen Complex/Nitroxyl Radical Catalysis — Yusuke Sasano, Shogo Fujiki, et al. · Chemical and Pharmaceutical Bulletin (2026) | TGRS Research Map | TGRS