2-Fluoropyridinium Salts Applicable to Deoxygenation Reactions of Alcohols

3-Cyclohexyl-2-fluoro-1-methylpyridine-1-ium trifluoromethanesulfonate (1), which was developed based on the Mukaiyama reagent, enables deoxygenation reactions of alcohols without the use of a catalyst.¹⁾ 1 forms an electron donor–acceptor (EDA) complex through reaction with the alcohol. Subsequent LED irradiation with visible light excitation triggers C-O bond cleavage and hydrogenation, thereby causing the deoxygenation reaction. This reaction does not require expensive metal catalysts and occurs under mild conditions. It is applicable to various amino alcohols, sugars, and steroids bearing primary and secondary hydroxy groups. Adding a radical acceptor to the reaction system also enables the formation of C-C bonds.²⁾
1 has been commercialized under the instruction of Dr. Takeshi Nanjo.

References

• 1) A Sterically Tuned 2-Fluoropyridinium Salt for the Catalyst-Free, Visible-Light-Mediated Deoxygenation of Alcohols via an Electron Donor–Acceptor Complex
  • T. Nanjo, Y. Lin, Y. Fujii, Y. Takemoto, Org. Lett. 2025, 27, 2616.
• 2) Visible Light-Induced Deoxygenation and Allylation/Vinylation of Pyridyl Ethers
  • F. Wang, Y. Tang, X. Li, J. Chen, J. Yang, Org. Lett. 2022, 24, 7309.

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