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Site-Selective C(sp3)-H Fluorination of Saccharides: Switching the Reaction Sites by Changing Fluorination Reagents
Erina Kurokawa1, Yanru Li1, Sakura Okuyama1
1Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan.
Abstract:
We successfully developed a method for the site-selective C(sp3)-H fluorination of saccharides. When saccharides were treated with Selectfluor under 405 nm light irradiation, fluorination selectively proceeded at the weakest C(sp3)-H bond. Conversely, when the same saccharides were treated with N-fluorobenzenesulfonimide in the presence of a sodium decatungstate catalyst under 365 nm light irradiation, the reaction site could be switched and fluorination occurred at the C(sp3)-H bond with less steric hindrance.
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