Iron-Catalyzed Oxidation of Thioethers by Iodosylarenes: Stereoselectivity and Reaction Mechanism Full article
| Journal |
Chemistry - A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765 |
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| Output data | Year: 2007, Volume: 13, Number: 28, Pages: 8045-8050 Pages count : 6 DOI: 10.1002/chem.200700566 | ||
| Tags | Asymmetric, Catalysis, Iron, Oxidation, Reaction mechanisms, Sulfoxides | ||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Russian Foundation for Basic Research | 06-03-32214 |
Abstract:
Catalytic properties of a series of iron(III)–salen (salen=N,N′-bis(salicylidene)ethylenediamine dianion) and related complexes in asymmetric sulfoxidation reactions, with iodosylarenes as terminal oxidants, have been explored. These catalysts have been found to efficiently catalyze oxidation of alkyl aryl sulfides to sulfoxides with high chemoselectivity (up to 100 %) and moderate-to-high enantioselectivity (up to 84 % with isopropylthiobenzene and iodosylmesitylene), the TON (TON=turnover number) approaching 500. The influence of the ligand (electronic and steric effects of the substituents), oxidant, and substrate structures on the oxidation stereoselectivity has been investigated systematically. The structure of the reactive intermediates (complexes of the type [FeIII(ArIO)(salen)] and the reaction mechanism have been revealed by both mechanistic studies with different iodosylarenes and direct in situ 1H NMR observation of the formation of the reactive species and its reaction with the substrate.
Cite:
Bryliakov K.P.
, Talsi E.P.
Iron-Catalyzed Oxidation of Thioethers by Iodosylarenes: Stereoselectivity and Reaction Mechanism
Chemistry - A European Journal. 2007. V.13. N28. P.8045-8050. DOI: 10.1002/chem.200700566 WOS Scopus РИНЦ ANCAN PMID OpenAlex
Iron-Catalyzed Oxidation of Thioethers by Iodosylarenes: Stereoselectivity and Reaction Mechanism
Chemistry - A European Journal. 2007. V.13. N28. P.8045-8050. DOI: 10.1002/chem.200700566 WOS Scopus РИНЦ ANCAN PMID OpenAlex
Dates:
| Submitted: | Apr 12, 2007 |
| Published online: | Jul 4, 2007 |
| Published print: | Sep 28, 2007 |
Identifiers:
| Web of science: | WOS:000250032300023 |
| Scopus: | 2-s2.0-35048854604 |
| Elibrary: | 13542096 |
| Chemical Abstracts: | 2007:1179670 |
| Chemical Abstracts (print): | 148:33459 |
| PMID: | 17611952 |
| OpenAlex: | W2151456957 |