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Synlett 1991; 1991(3): 185-186
DOI: 10.1055/s-1991-20672
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Dilute Hydrofluoric Acid as a Fluorinating Agent: Iodofluorination of Olefins with Dilute Hydrofluoric Acid, N-Iodosuccinimide, and a Phase Transfer Catalyst

Manabu Kuroboshi* , Tamejiro Hiyama
  • *Sagami Chemical Research Center, 4-4-1 Nishiohnuma, Sagamihara, Kanagawa 229, Japan
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Publication Date:
07 March 2002 (online)

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Regio-, stereo-, and chemoselective iodofluorination of olefins is readily effected under a two-phase system using dilute hydrofluoric acid, N-iodosuccinimide, and tetrabutylammonium fluoride as a phase transfer catalyst. Additional use of potassium hydrogen fluoride (KHF2) enhanced the yields of fluoro-iodo adducts and suppressed the formation of iodohydrins as byproducts.