Kinetics and enantioselectivity of the Baeyer-Villiger oxidation of cyclohexanones by chiral tetrapyridyl oxoiron(IV) complex

The previously reported oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, asN4Py (asN4Py = N,N‑bis(2‑pyridylmethyl)‑1,2‑di(2‑pyridyl)ethylamine), is effective for the Baeyer-Villiger oxidation of cyclohexanone derivatives. The reaction is shown to be first order in both cyclo...

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Bibliographic Details
Published in:Inorganic chemistry communications 2018-06, Vol.92, p.141-144
Main Authors: Turcas, Ramona, Lakk-Bogáth, Dóra, Speier, Gábor, Kaizer, József
Format: Article
Language:English
Subjects:
Baeyer-Villiger oxidation
Biomimetics
Enantioselectivity
Iron(IV)-oxo complex
Kinetics
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Summary:The previously reported oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, asN4Py (asN4Py = N,N‑bis(2‑pyridylmethyl)‑1,2‑di(2‑pyridyl)ethylamine), is effective for the Baeyer-Villiger oxidation of cyclohexanone derivatives. The reaction is shown to be first order in both cyclohexanone and the oxoiron(IV) species. The second order rate constant is smaller by one order of magnitude than that obtained for the related achiral [FeIV(N4Py)(O)]2+ complex. Oxidation of 4-substituted cyclohexanone derivatives by the chiral oxoiron(IV) complex attains moderate enantioselectivities up to 45% enantiomeric excess (ee). The reactivity of oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, has been investigated in the Baeyer-Villiger oxidation of cyclohexanone derivatives. [Display omitted] •Reactivity of chiral oxoiron(IV) complex towards cyclohexanone.•Reaction kinetics with UV–Vis spectroscopy.•Enantioselective Baeyer-Villiger reactions.
ISSN:1387-7003
1879-0259
DOI:10.1016/j.inoche.2018.04.024