Iron(III) Trifluoroacetate as an Efficient Catalyst for Solvolytic and Nonsolvolytic Nucleophilic Ring Opening of Epoxides

Abstract

Iron(III) trifluoroacetate was used as an efficient and nonhygroscopic catalyst for the alcoholysis, hydrolysis, and acetolysis of epoxides. The addition of chloride, bromide, iodide, and nitrate ions to epoxides to produce the corresponding 2-halo and 2-nitratoalkanols and also the conversion of epoxides to acetonides and thiiranes were also performed efficiently in the presence of this catalyst.

Controlling Selectivity in Alkene Oxidation: Anion Driven Epoxidation or Dihydroxylation Catalysed by [Iron(III)(Pyridine‐Containing Ligand)] Complexes

“…[25] Among the catalysts used, both Fe(OTf) 3 [26] and anhydrous FeCl 3 [27] salts were reported to promote this reaction with good yields. Epoxides can be readily converted into acetonides in the presence of catalytic amounts of Lewis acids in acetone as solvent.…”

Well-defined epoxide-containing styrenic polymers and their functionalization with alcohols

“…Heterogeneous acidic catalysts that have been successfully employed for this purpose include sulfonated polymers (Amberlyst‐15 and Nafion‐H), neutral alumina, mesoporous aluminosilicate, organotin phosphate condensates (OPCs), and Fe 3+ ‐montmorillonite, but it is unlikely that they could achieve sufficient interaction with the pendant functionalities of polymers to efficiently promote functionalization. Soluble compounds or complexes of main group metals, transition metals, and lanthanides are well‐known for their Lewis acidity and have been investigated specifically for their ability to catalyze the alcoholysis of epoxides. The catalytic activities of non‐metallic Lewis acids like BF 3 , CBr 4 , hydrazine sulphate, molecular iodine, iminium triflate, and trimethylsilyl triflate, as well as compounds able to participate in single‐electron reactions like 2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone, tetracyanoethylene, ceric ammonium nitrate, N ‐methylpyrrolidine‐2‐one hydrotribromide, and 1‐benzyl‐2,4,6‐triphenylpyridinium tetrafluoroborate, have also been explored.…”

Facile protection of carbonyl compounds as oxathiolanes and transoxathioacetalization of oxyacetals promoted by iron(III) trifluoroacetate or trifluoromethanesulfonate as chemoselective and recyclable catalysts

“…Iron(III) trifluoroacetate [6] and iron(III) trifluoromethanesulfonate [7] were prepared according to reported procedures. Yields refer to isolated products after purification.…”

“…Recently, we reported that solvolytic and non-solvolytic ring-opening reactions of epoxides are facilitated in the presence of iron(III) trifluoroacetate [6]. Also, iron(III) triflate is a novel Lewis acid, which has attracted little attention as a catalyst [7].…”