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Metal-Free Fluorination of C(sp3)-H Bonds Using a Catalytic N-Oxyl Radical

Yuuki Amaoka, Masanori Nagatomo and Masayuki Inoue*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: inouemol.f.u-tokyo.ac.jp

Y. Amaoka, M. Nagamoto, M. Inoue, Org. Lett., 2013, 15, 2160-2163.

DOI: 10.1021/ol4006757 (free Supporting Information)


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Abstract

In a direct fluorination of C(sp3)-H bonds, a catalytic N-oxyl radical generated from N,N-dihydroxypyromellitimide abstracts the hydrogen followed by trapping of the resulting carbon radical by Selectfluor. This simple metal-free protocol enables the chemoselective introduction of a fluorine atom into various aromatic and aliphatic compounds and serves as a powerful tool for the efficient synthesis of fluorinated molecules.


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Key Words

fluorination, Selectfluor


ID: J54-Y2013