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Hypervalent Iodine-Mediated Fluorination of Styrene Derivatives: Stoichiometric and Catalytic Transformation to 2,2-Difluoroethylarenes

Tsugio Kitamura*, Kensuke Muta and Juzo Oyamada

*Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan, Email: kitamuracc.saga-u.ac.jp

T. Kitamura, K. Muta, J. Oyamada, J. Org. Chem., 2015, 80, 10431-10436.

DOI: 10.1021/acs.joc.5b01929 (free Supporting Information)


 

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Abstract

Fluorination of styrene derivatives with a reagent system composed of μ-oxo-bis[trifluoroacetato(phenyl)iodine] or PhI(OCOCF3)2 and a pyridine·HF complex gave the corresponding (2,2-difluoroethyl)arenes in good yields. Catalytic conditions using 4-iodotoluene as a catalyst and m-CPBA as a terminal oxidant are possible.

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Key Words

difluoroalkanes, PIFA


ID: J42-Y2015