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Halogen Exchange Reaction of Aliphatic Fluorine Compounds with Organic Halides as Halogen Source

Yuki Mizukami, Zhiyi Song and Tamotsu Takahashi*

*Catalysis Research Center and Graduate School of Life Science, Hokkaido University, Kita-ku, Sapporo 001-0021, Japan, Email: tamotsucat.hokudai.ac.jp

Y. Mizukami, Z. Song, T. Takahashi, Org. Lett., 2015, 17, 5942-5945.

DOI: 10.1021/acs.orglett.5b02589 (free Supporting Information)


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Abstract

Treatment of primary, secondary, or tertiary alkyl fluorides with a catalytic amount of titanocene dihalides, trialkyl aluminum, and polyhalomethanes as the halogen source achieves a halogen exchange reaction in excellent yields under mild conditions. In the case of a fluorine/iodine exchange, no titanocene catalyst is needed. Only C-F bonds are activated under these conditions, whereas alkyl chlorides, bromides, and iodides remained intact.

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Key Words

alkyl iodides, alkyl bromides


ID: J54-Y2015