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Difluorination of Functionalized Aromatic Olefins Using Hypervalent Iodine/HF Reagents

Tsugio Kitamura*, Kento Yoshida, Shota Mizuno, Azusa Miyake, Juzo Oyamada

*Department of Chemistry and Applied Chemistry, Saga University, 1 Honjo-machi, Saga 840-8502, Japan, Email:

T. Kitamura, K. Yoshida, S. Mizuno, A. Miyake, J. Oyamada, J. Org. Chem., 2018, 83, 14834-14841.

DOI: 10.1021/acs.joc.8b02473 (free Supporting Information)

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The combination of PhIO and HF·py enables fluorination of functionalized aromatic olefins bearing synthetically important carbonyl and hydroxyl groups. Fluorination of for example 1,3-diphenyl-2-propen-1-one with PhIO/HF·py reagent gave 3,3-difluoro-1,2-diphenyl-1-propanone in high yield. The fluorination of cinnamyl alcohol derivatives proceeded smoothly to afford 2-aryl-3,3-difluoro-1-propanols in moderate yields.

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Key Words

difluorination, iodosylbenzene

ID: J42-Y2018