NDLI: Highly selective hydroxylation of alkanes catalyzed by (μ-oxo)bis(μ-carboxylato)-bridged diiron(iii) complexes: involvement of mononuclear iron(iii) species in catalysis

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Highly selective hydroxylation of alkanes catalyzed by (μ-oxo)bis(μ-carboxylato)-bridged diiron(iii) complexes: involvement of mononuclear iron(iii) species in catalysis

Content Provider	Royal Society of Chemistry (RSC)
Author	Suresh, Eringathodi Visvaganesan, Kusalendiran Palaniandavar, Mallayan
Copyright Year	2009
Abstract	A few diiron(III) complexes [Fe2(O)(OAc)2(L1)2](ClO4)21, [Fe2(O)(OBz)2(L1)2](ClO4)22, [Fe2(O)(OAc)2(L2)2](ClO4)23 and [Fe2(O)(OBz)2(L2)2](ClO4)24, where L1 = N,N-bis(pyrid-2-ylmethyl)-iso-butylamine, L2 = N,N-bis(pyrid-2-ylmethyl)benzylamine, AcO = acetate and BzO = benzoate, have been isolated and characterized by means of elemental analysis and spectral and electrochemical methods. The molecular structures of the complexes 2 and 4 have been determined by single-crystal X-ray diffraction analysis and they possess a distorted bioctahedral geometry in which each iron atom is coordinated to the oxygen atom of the μ-oxo bridge, two oxygen atoms of the μ-benzoato bridges and three nitrogen atoms of L1 and L2 ligands capping the two ends of the diiron(III) cluster. The ESI-MS spectral data of the complexes reveal that the complexes remain intact in dichloromethane (DCM) solution. Upon adding one equivalent of Et3N to a mixture of one equivalent of the diiron(III) complexes and excess of m-chloroperbenzoic acid (m-CPBA) in DCM, an intense absorption band (λmax, 670–700 nm) appears, which corresponds to the species [Fe2(O)(OAc)(m-CPBA)(L)2]2+ (ESI-MS, m/z 466) suggested as the intermediate involved in the oxygenation reactions. All the present complexes show efficient alkane hydroxylation with 300–400 turn over numbers and good selectivities for cyclohexane (A/K, 10–14) and adamantane (3°/2°, 9–11). Interestingly, the formation of monoiron(III) species has been discerned in the alkane hydroxylation reactions beyond ∼50 turnovers. The mononuclear 1 : 1 iron(III) complexes of L1 and L2 ligands generated in situ are also found to catalyze the oxygenation reactions with high selectivity and efficiency for cyclohexane (A/K, 10–14). Upon their reaction with m-CPBA in DCM, a characteristic absorption band (λmax, 600 nm, εmax, 355 M−1 cm−1) appears and decays at room temperature. This spectral feature is consistent with the mononuclear high-valent iron-oxo species suggested as an intermediate in the oxygenation reactions.
Starting Page	3814
Ending Page	3823
Page Count	10
File Format	HTM / HTML PDF
ISSN	14779226
Volume Number	0
Issue Number	19
Journal	Dalton Transactions
DOI	10.1039/b901508f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Benzylamine Benzoic acid Electrochemistry X-ray crystallography Molecular geometry Nitrogen Dichloromethane Carboxylic acid Meta-Chloroperoxybenzoic acid Absorption band Hydroxylation Cyclohexane Adamantane
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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