PIFA

Technical Specifications

Product Description & Scientific Applications

PIFA (phenyliodine(III) bis(trifluoroacetate); iodobenzene bis(trifluoroacetate), PhI(OCOCF3)2) is the trifluoroacetate hypervalent iodine(III) oxidant (C10H5F6IO4, 430.04 g/mol) — the same iodine(III) centre as PIDA, with trifluoroacetate ligands in place of acetates.

That substitution is what changes the chemistry: PIFA oxidises electron-rich arenes by single electron transfer, generating aromatic cation radicals from phenyl ethers.

Handling it is undemanding. It can be weighed and charged in air without special technique — hydrolysis of the trifluoroacetate ligands is slow on that timescale. What matters is the months between uses, not the minutes on the balance: keep the bottle tightly closed and dry, cold and out of the light. Inert gas extends shelf life but is not required to use the reagent.

Applications and Reactions

• Oxidative biaryl coupling: couples pyrroles to α-linked bipyrroles in the presence of bromotrimethylsilane, a metal-free route to biaryl bonds.
• Heterocycle synthesis: intramolecular cyclisation gives N-arylated and N-alkylated indoles, and intramolecular oxidative N–N bond formation converts benzimidamides to 1,2,4-triazolo[1,5-a]pyridines.
• Oxidative C–C bond formation: with anilides in trifluoroethanol it gives 3-hydroxy-2-oxindoles, and it rearranges 1-arylamino-2-oxocyclopentanecarbonitriles to N-aryl-δ-valerolactams.
• C–H functionalisation: effects direct acetoxylation and etherification of anilides, and C–H selenylation of benzimidazothiazoles with broad functional-group tolerance.
• Remote C–H functionalisation: as the sole reagent it enables alcohol-directed regioselective heteroarylation of remote unactivated C–H bonds, and under mild photochemical conditions it generates alkoxy radicals for remote alkynylation and allylation.
• Controllable chlorination: with tetrabutylammonium chloride, stoichiometry selects 3-chloroindoles, 3-chloro-2-oxindoles or 3,3-dichloro-2-oxindoles.
• Chlorophyll modification: with iodine it converts a C3-vinyl group to acetyl, epoxy or formyl.
• Storage: tightly closed and dry, cold and dark. Inert gas recommended for long-term storage.

Shipping Destinations

• EU & UK: Priority delivery, 2–5 business days.
• United States (DDP): 3–7 business days, duties and taxes prepaid.
• EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
• Worldwide: 7–14 business days, selected locations.