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Article: Iron oligopyridine complexes as efficient catalysts for practical oxidation of arenes, alkanes, tertiary amines and N-acyl cyclic amines with Oxone

TitleIron oligopyridine complexes as efficient catalysts for practical oxidation of arenes, alkanes, tertiary amines and N-acyl cyclic amines with Oxone
Authors
KeywordsC-c bonds
C-h bond
Catalyse
Cross coupling reactions
Cyclic amines
Issue Date2011
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/publishing/journals/sc/About.asp
Citation
Chemical Science, 2011, v. 2 n. 11, p. 2187-2195 How to Cite?
AbstractThe iron complexes [Fe(qpy)](ClO 4) 2 (1) (qpy = 2, 2′:6′, 2′′:6′′, 2′′′: 6′′′, 2′′′′-quinquepyridine), [Fe 2(spy) 2](ClO 4) 4 (2) (spy = 2, 2′:6′, 2′′:6′′, 2′′′: 6′′′, 2′′′′: 6′′′ ′, 2′′′′′-sexipyridine), [Fe 2(septipy) 2](ClO 4) 4 (3) (septipy = 2, 2′:6′, 2′′:6′′, 2′′′: 6′′′, 2′′′′: 6′′′′, 2′′′′′: 6′′′′′, 2′′′′′ ′-septipyridine) and SBA-15-supported iron terpyridine complex (4) are efficient catalysts for the practical oxidation of alkenes, arenes, alkanes, tertiary amines and N-acyl cyclic amines using Oxone as the oxidant. With 1, 2, 3 or 4 as the catalyst, a variety of electron-rich and electron-deficient alkenes were oxidized to the corresponding epoxides in high isolated yields (up to 99%). The reaction of arenes with Oxone afforded quinones in up to 91% isolated yields. Selective C-H bond oxidation of saturated alkanes to alcohols/ketones and demethylation of tertiary amines to secondary amines were achieved in good product yields. For the oxidation of N-acyl cyclic amines, the ring-opened products were obtained in up to 75% isolated yield with up to 96% substrate conversion. All of these iron complexes can efficiently catalyse the oxidative C-C bond cross-coupling reaction of tertiary amines with NaCN in up to 86% isolated yield using ( tBuO) 2 as the terminal oxidant. The oligopyridine ligands were oxidatively robust and could be re-used by the addition of iron(ii) salt to generate the iron catalysts in situ. The active SBA-15-supported terpy ligand could be re-used for the oxidative catalysis for five consecutive runs without significant loss of catalytic activity. © The Royal Society of Chemistry 2011.
Persistent Identifierhttp://hdl.handle.net/10722/152641
ISSN
2015 Impact Factor: 9.144
2015 SCImago Journal Rankings: 4.974
ISI Accession Number ID
Funding AgencyGrant Number
Hong Kong Research Grants CouncilHKU 1/CRF/08
HKU 700810
University Grants Committee of the Hong Kong Special Administrative Region, ChinaAoE 10/01P
Funding Information:

This work was supported by the Hong Kong Research Grants Council (HKU 1/CRF/08 and HKU 700810) and the Areas of Excellence Scheme established under the University Grants Committee of the Hong Kong Special Administrative Region, China (AoE 10/01P).

References

 

DC FieldValueLanguage
dc.contributor.authorLiu, Pen_HK
dc.contributor.authorLiu, Yen_HK
dc.contributor.authorWong, ELMen_HK
dc.contributor.authorXiang, Sen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2012-07-16T09:44:49Z-
dc.date.available2012-07-16T09:44:49Z-
dc.date.issued2011en_HK
dc.identifier.citationChemical Science, 2011, v. 2 n. 11, p. 2187-2195en_HK
dc.identifier.issn2041-6520en_HK
dc.identifier.urihttp://hdl.handle.net/10722/152641-
dc.description.abstractThe iron complexes [Fe(qpy)](ClO 4) 2 (1) (qpy = 2, 2′:6′, 2′′:6′′, 2′′′: 6′′′, 2′′′′-quinquepyridine), [Fe 2(spy) 2](ClO 4) 4 (2) (spy = 2, 2′:6′, 2′′:6′′, 2′′′: 6′′′, 2′′′′: 6′′′ ′, 2′′′′′-sexipyridine), [Fe 2(septipy) 2](ClO 4) 4 (3) (septipy = 2, 2′:6′, 2′′:6′′, 2′′′: 6′′′, 2′′′′: 6′′′′, 2′′′′′: 6′′′′′, 2′′′′′ ′-septipyridine) and SBA-15-supported iron terpyridine complex (4) are efficient catalysts for the practical oxidation of alkenes, arenes, alkanes, tertiary amines and N-acyl cyclic amines using Oxone as the oxidant. With 1, 2, 3 or 4 as the catalyst, a variety of electron-rich and electron-deficient alkenes were oxidized to the corresponding epoxides in high isolated yields (up to 99%). The reaction of arenes with Oxone afforded quinones in up to 91% isolated yields. Selective C-H bond oxidation of saturated alkanes to alcohols/ketones and demethylation of tertiary amines to secondary amines were achieved in good product yields. For the oxidation of N-acyl cyclic amines, the ring-opened products were obtained in up to 75% isolated yield with up to 96% substrate conversion. All of these iron complexes can efficiently catalyse the oxidative C-C bond cross-coupling reaction of tertiary amines with NaCN in up to 86% isolated yield using ( tBuO) 2 as the terminal oxidant. The oligopyridine ligands were oxidatively robust and could be re-used by the addition of iron(ii) salt to generate the iron catalysts in situ. The active SBA-15-supported terpy ligand could be re-used for the oxidative catalysis for five consecutive runs without significant loss of catalytic activity. © The Royal Society of Chemistry 2011.en_HK
dc.languageengen_US
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/publishing/journals/sc/About.aspen_HK
dc.relation.ispartofChemical Scienceen_HK
dc.subjectC-c bonds-
dc.subjectC-h bond-
dc.subjectCatalyse-
dc.subjectCross coupling reactions-
dc.subjectCyclic amines-
dc.titleIron oligopyridine complexes as efficient catalysts for practical oxidation of arenes, alkanes, tertiary amines and N-acyl cyclic amines with Oxoneen_HK
dc.typeArticleen_HK
dc.identifier.emailLiu, P: harrylau@hku.hken_HK
dc.identifier.emailLiu, Y: lyg100@hku.hken_HK
dc.identifier.emailWong, ELM: wongella@hku.hken_HK
dc.identifier.emailXiang, S: sxiang@hkucc.hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hk-
dc.identifier.authorityLiu, Y=rp00749en_HK
dc.identifier.authorityWong, ELM=rp00807en_HK
dc.identifier.authorityXiang, S=rp00816en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/c1sc00234aen_HK
dc.identifier.scopuseid_2-s2.0-81355139632en_HK
dc.identifier.hkuros201648en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-81355139632&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume2en_HK
dc.identifier.issue11en_HK
dc.identifier.spage2187en_HK
dc.identifier.epage2195en_HK
dc.identifier.isiWOS:000295732200016-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridXiang, S=36194404300en_HK
dc.identifier.scopusauthoridWong, ELM=8944839700en_HK
dc.identifier.scopusauthoridLiu, Y=8225912600en_HK
dc.identifier.scopusauthoridLiu, P=36727836300en_HK

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