The Iron(II) Complex [Fe(CF₃SO₃)₂(mcp)] as a Convenient, Readily Available Catalyst for the Selective Oxidation of Methylenic Sites in Alkanes

Abstract

The efficient and selective oxidation of secondary C À H sites of alkanes is achieved by using low catalyst loadings of a non-expensive, readily available iron catalyst [Fe(II)-trans-1,2-diamine]}, and hydrogen peroxide (H 2 O 2 ) as oxidant, via a simple reaction protocol. Natural products are selectively oxidized and isolated in synthetically amenable yields. The easy access to large quantities of the catalyst and the simplicity of the C À H oxidation procedure make this system a particularly convenient tool to carry out alkane C À H oxidation reactions on the preparative scale, and in short reaction times.

New Trends in Oxidative Functionalization of Carbon–Hydrogen Bonds: A Review

“…However, in catalyst systems relying on isostructural Fe catalysts, such evidence was gained by EPR spectroscopy taking advantage of the low-spin (S = 1 / 2 ) structure of known oxoiron(V) intermediates [189]. Costas in recent years has carried out many valuable works on functionalization of carbon-hydrogen bond catalyzed by nonheme complexes with polyamino ligands [190][191][192][193]. Additionally, very important works on complexes with polydentate ligands as catalysts have been reported by Nam and colleagues [194].…”

Molecular iron complexes as catalysts for selective C–H bond oxygenation reactions

“…Furthermore, the oxidation of complex organic molecules under mild conditions was achieved with good yields using chiral iron complexes of ligands 19b, 22b and 22c. 73,74 (-)-Ambroxide for example was oxidised with H2O2 under similar conditions applied by Chen and White 68 but with lower catalyst loadings (Scheme 5). The selectivity of the reactions turned out to be guided by the spacial structure of the iron active site as well as the structural and electronic properties of the substrates.…”

C–H benzylic oxidation promoted by dinuclear iron DBDOC iminopyridine complexes

“…Also in 1997, Nishida and co-workers reported N 1 ,N 2 -dimethyl-N 1 ,N 2 -bis(pyridin-2-ylmethyl)ethane-1,2-diamine (BPMEN) as a convenient ligand system for iron promoted oxidations [13]. Modification of BPMEN resulted in interesting ligands for iron catalyzed C-H bond oxidations [14][15][16]. The two main structures of tetradentate ligands in iron catalyzed oxidation of alkanes are derived from TPA and BPMEN, having tripodal and linear structures, respectively [17].…”