A StericallyTuned 2‑Fluoropyridinium Saltfor the Catalyst-Free, Visible-Light-Mediated Deoxygenation of Alcoholsvia an Electron Donor–Acceptor Complex

We here report the use of a sterically tuned 2-fluoro-1-methylpyridinium salt for the catalyst-free, visible-light-mediated deoxygenative transformation of alcohols through alkoxypyridinium intermediates. The key to this process is the introduction of a bulky cyclohexyl group at the 3-position of the pyridinium ring, which enforces a favorable conformation for C–O bond cleavage and the formation of an electron donor–acceptor complex between the pyridinium ring and amines.

Publication Details

Journal
Figshare
Published
2025-03-07
DOI
https://doi.org/10.1021/acs.orglett.5c00266.s001
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

A StericallyTuned 2‑Fluoropyridinium Saltfor the Catalyst-Free, Visible-Light-Mediated Deoxygenation of Alcoholsvia an Electron Donor–Acceptor Complex

Figshare
Radical Photochemical Reactions
article

A StericallyTuned 2‑Fluoropyridinium Saltfor the Catalyst-Free, Visible-Light-Mediated Deoxygenation of Alcoholsvia an Electron Donor–Acceptor Complex

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Abstract

We here report the use of a sterically tuned 2-fluoro-1-methylpyridinium salt for the catalyst-free, visible-light-mediated deoxygenative transformation of alcohols through alkoxypyridinium intermediates. The key to this process is the introduction of a bulky cyclohexyl group at the 3-position of the pyridinium ring, which enforces a favorable conformation for C–O bond cleavage and the formation of an electron donor–acceptor complex between the pyridinium ring and amines.

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Radical Photochemical Reactions
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A StericallyTuned 2‑Fluoropyridinium Saltfor the Catalyst-Free, Visible-Light-Mediated Deoxygenation of Alcoholsvia an Electron Donor–Acceptor Complex · Figshare (2025) | TGRS Research Map | TGRS