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Aliphatic C-H Bond Halogenation by Iron(II)-α-Keto Acid Complexes and O 2 : Functional Mimicking of Nonheme Iron Halogenases.
- Source :
-
Inorganic chemistry [Inorg Chem] 2018 Aug 06; Vol. 57 (15), pp. 8769-8777. Date of Electronic Publication: 2018 Jul 16. - Publication Year :
- 2018
-
Abstract
- α-Ketoglutarate-dependent nonheme halogenases catalyze the halogenation of aliphatic C-H bonds in the biosynthesis pathway of many natural products. An iron(IV)-oxo-halo species has been established as the active oxidant in the halogenation reactions. With an objective to emulate the function of the nonheme halogenases, two iron(II)-α-keto acid complexes, [(phdpa)Fe(BF)Cl] (1) and [(1,4-tpbd)Fe <subscript>2</subscript> (BF) <subscript>2</subscript> Cl <subscript>2</subscript> ] (2) (where phdpa = N,N-bis(2-pyridylmethyl)aniline, 1,4-tpbd = N,N, N',N'-tetrakis(2-pyridylmethyl)benzene-1,4-diamine, and BF = benzoylformate), have been prepared. The iron complexes are capable of carrying out the oxidative halogenation of aliphatic C-H bonds using O <subscript>2</subscript> as the terminal oxidant. Although the complexes are not selective toward C-H bond halogenation, they are the only examples of nonheme iron(II)-α-keto acid complexes mimicking the activity of nonheme halogenases. The dinuclear complex (2) exhibits enhanced reactivity toward C-H bond halogenation/hydroxylation.
Details
- Language :
- English
- ISSN :
- 1520-510X
- Volume :
- 57
- Issue :
- 15
- Database :
- MEDLINE
- Journal :
- Inorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30009593
- Full Text :
- https://doi.org/10.1021/acs.inorgchem.8b00421