Home > Exhibitions / Brochures Download > New Stable Fluorinating Reagent with Ease of Handling (Hara Reagent)

New Stable Fluorinating Reagent with Ease of Handling (Hara Reagent)

IF5-Pyridine-HF (P2140), which was first reported by Hara et al., is a novel fluorinatingreagent. Pentafluoroiodide (IF5) is a strong fluorination liquid agent, but it is unstable in airand decomposes, generating HF. P2140 is a crystalline solid reagent with air stability andnon-hygroscopicity which makes it easier to handle, and can be used as an alternativereagent to IF5. P2140 can be applied to various fluorination reactions of sulfides asfollows.1-4) In addition, P2140 iodofluorinates alkenes with streo- and regioselectivity.5)

Advantages

・Air-Stable and Non-Hygroscopic Crystalline
・Easy to Handle
・Widely Applicable to Various Fluorinations of Suldes

Fluorination of the α-Positon of a Sulde 1)

Application Example (first reaction formula)
To a CH2Cl2 solution (2 mL) of ethyl 2-[(4-chlorophenyl)thio]propanoate (122 mg, 0.5 mmol) is added P2140 (370 mg,1.15 mmol) at room temperature, and the mixture is stirred at room temperature for 24 h. The resulting dark red solution is poured into water (20 mL) and extracted with CH2Cl2 (20 mL x 3). The combined organic layer is washed with aq. NaHCO3 and aq. Na2S2O3, and dried over MgSO4. After concentration under reduced pressure, the residue is purified with silica gel column chromatography (eluent: hexane/ether) to give ethyl 2-[(4-chlorophenyl)thio]-2-fluoropropanoate in 89% yield (117 mg).

Reference

  • 1) S. Hara, M. Monoi, R. Umemura, C. Fuse, Tetrahedron 2012, 68, 10145.

Other Applications

Desulfurizing-Difluorination of Aldehyde and Ketone Dithioacetals1)

Trifluoromethylation of Aldehyde Thioacetal Derivatives1)

Desulfurizing-Fluorination of Methylthiomethyl Ethers and Esters2)

Conversion of Dithiocarbonates to OCF2SCH3 or OCF33)

Synthesis of Glycosyl Fluorides from (Phenylthio)glycosides4)

Iodofluorination of Alkenes5)

Reference

  • 1) S. Hara, M. Monoi, R. Umemura, C. Fuse, Tetrahedron 2012, 68, 10145.
  • 2) M. Kunigami, S. Hara, J. Fluorine Chem. 2014, 167, 101.
  • 3) T. Inoue, C. Fuse, S. Hara, J. Fluorine Chem. 2015, 179, 48.
  • 4) M. Kunigami, S. Hara, Carbohydr. Res. 2015, 417, 78.
  • 5) S. Yano, S. Hara, Synthesis 2015, 2839.

This reagent was merchandised under the tie-up with DAIKIN INDUSTRIES, LTD.

Page Top