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A Sterically Tuned 2-Fluoropyridinium Salt for the Catalyst-Free, Visible-Light-Mediated Deoxygenation of Alcohols via an Electron Donor–Acceptor Complex

2025/03/07 by Takeshi Nanjo, Yixuan Lin, Yuki Fujii +1 · 1 voice
Chemistry · #Radical Photochemical Reactions #Oxidative Organic Chemistry Reactions #Sulfur-Based Synthesis Techniques

paper · doi:10.1021/acs.orglett.5c00266

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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