In situ-generated chiral iron complex as efficient catalyst for enantioselective sulfoxidation using aqueous H 2 O 2 as oxidant

A series of amino alcohol-derived, Schiff-base ligands L1–L4 were synthesised and characterized. Iron complexes of these ligands [Fe L1 (acac)], [Fe L2 (acac)], [Fe L3 (acac)] and [Fe L4 (acac)] were generated in situ to catalyze the asymmetric oxidation of prochiral sulfides using aqueous H 2 O 2 a...

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Bibliographic Details
Published in:RSC advances 2014, Vol.4 (106), p.61550-61556
Main Authors: Bera, Prasanta Kumar, Kumari, Prathibha, Abdi, Sayed H. R., Khan, Noor-ul H., Kureshy, Rukhsana I., Subramanian, P. S., Bajaj, Hari C.
Format: Article
Language:English
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Summary:A series of amino alcohol-derived, Schiff-base ligands L1–L4 were synthesised and characterized. Iron complexes of these ligands [Fe L1 (acac)], [Fe L2 (acac)], [Fe L3 (acac)] and [Fe L4 (acac)] were generated in situ to catalyze the asymmetric oxidation of prochiral sulfides using aqueous H 2 O 2 as a terminal oxidant. One of these complexes [Fe L1 (acac)] was identified as a very efficient catalyst for the enantioselective oxidation of a series of alkyl aryl sulfides with excellent enantioselectivity (75–96% ee), conversion (up to 92%) and chemo selectivity (up to 98%). During the optimization process, a series of electron-donating benzoic acid derivatives were found to favour both conversion and enantioselectivity.
ISSN:2046-2069
2046-2069
DOI:10.1039/C4RA09237F