Fe(III)-Catalyzed Highly Efficient Oxidative Cross-Coupling of 2-Naphthols and 2,6-Dihydroxynaphthalene with Furans

Catalytic oxidative cross-coupling has emerged as a vital tool for C-C bond formation. Herein, we disclose a hitherto unknown highly efficient catalytic oxidative cross-coupling of furans with 2-naphthols and 2,6-dihydroxynaphthalene using an earth-abundant Fe(III) catalyst. The methodology is characterized by exquisite chemoselectivity in oxidation, high cross-selectivity in coupling, excellent functional group tolerance, and a broad substrate scope. Mechanistic studies indicate chemoselective oxidation of naphthol in the presence of furan, despite their comparable oxidation potentials (Δ<i>E</i><sub>ox</sub> of 0.15 V).

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Publication Details

Journal
Organic Letters
Published
2025-12-18
DOI
https://doi.org/10.1021/acs.orglett.5c03491
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
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article

Fe(III)-Catalyzed Highly Efficient Oxidative Cross-Coupling of 2-Naphthols and 2,6-Dihydroxynaphthalene with Furans

Rishikesh Narayan, Shon Gangai, D. G. Naik, Deepak Datta Gaonkar
Organic Letters
Axial and Atropisomeric Chirality Synthesis
article

Fe(III)-Catalyzed Highly Efficient Oxidative Cross-Coupling of 2-Naphthols and 2,6-Dihydroxynaphthalene with Furans

Rishikesh Narayan, Shon Gangai, D. G. Naik, Deepak Datta Gaonkar
article en

Abstract

Catalytic oxidative cross-coupling has emerged as a vital tool for C-C bond formation. Herein, we disclose a hitherto unknown highly efficient catalytic oxidative cross-coupling of furans with 2-naphthols and 2,6-dihydroxynaphthalene using an earth-abundant Fe(III) catalyst. The methodology is characterized by exquisite chemoselectivity in oxidation, high cross-selectivity in coupling, excellent functional group tolerance, and a broad substrate scope. Mechanistic studies indicate chemoselective oxidation of naphthol in the presence of furan, despite their comparable oxidation potentials (Δ<i>E</i><sub>ox</sub> of 0.15 V).

Organic LettersVol. 28(1)
Division of Materials Research (US), Indian Institute of Technology Goa (IN), Life University (US)
Openalex Percentile: Top 69%
Axial and Atropisomeric Chirality Synthesis
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Fe(III)-Catalyzed Highly Efficient Oxidative Cross-Coupling of 2-Naphthols and 2,6-Dihydroxynaphthalene with Furans — Rishikesh Narayan, Shon Gangai, et al. · Organic Letters (2025) | TGRS Research Map | TGRS