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Conference Paper: Practical iron-catalyzed atom/group transfer and insertion reactions

TitlePractical iron-catalyzed atom/group transfer and insertion reactions
Authors
KeywordsAmidation
Atom/Group Transfer
Catalysis
Iron
Oxidation
Issue Date2012
PublisherInternational Union of Pure and Applied Chemistry. The Journal's web site is located at http://www.iupac.org/publications/pac/
Citation
The 16th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-16), Shanghai, China, 24–28 July 2011. In Pure and Applied Chemistry, 2012, v. 84 n. 8, p. 1685-1704 How to Cite?
AbstractIron-catalyzed reactions are receiving a surge of interest owing to the natural abundance and biocompatibility of Fe and the urge to develop practically useful sustainable catalysis for fine chemical industries. This article is a brief account of our studies on the C-O and C-N bond formation reactions catalyzed by Fe complexes supported by oligopyridine, macrocyclic tetraaza, and fluorinated porphyrin ligands. The working principle is the in situ generation of reactive Fe=O and Fe=NR intermediates supported by these oxidatively robust N-donor ligands for oxygen atom/nitrogen group transfer and insertion reactions. The catalytic reactions include C-H bond oxidation of saturated hydrocarbons (up to 87 % yield), epoxidation of alkenes (up to 96 % yield), cis-dihydroxylation of alkenes (up to 99 % yield), epoxidation-isomerization (E-I) reaction of aryl alkenes (up to 94 % yield), amination of C-H bonds (up to 95 % yield), aziridination of alkenes (up to 95 % yield), sulfimidation of sulfides (up to 96 % yield), and amide formation from aldehydes (up to 89 % yield). Many of these catalytic reactions feature high regio- and diastereoselectivity and/or high product yields and substrate conversions, and recyclability of the catalyst, demonstrating the applicability of Fe-catalyzed oxidative organic transformation reactions in practical organic synthesis. © 2012 IUPAC.
Persistent Identifierhttp://hdl.handle.net/10722/168663
ISSN
2015 Impact Factor: 2.615
2015 SCImago Journal Rankings: 0.912
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorChow, TWS-
dc.contributor.authorChen, GQ-
dc.contributor.authorLiu, Y-
dc.contributor.authorZhou, CY-
dc.contributor.authorChe, CM-
dc.date.accessioned2012-10-08T03:24:09Z-
dc.date.available2012-10-08T03:24:09Z-
dc.date.issued2012-
dc.identifier.citationThe 16th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-16), Shanghai, China, 24–28 July 2011. In Pure and Applied Chemistry, 2012, v. 84 n. 8, p. 1685-1704-
dc.identifier.issn0033-4545-
dc.identifier.urihttp://hdl.handle.net/10722/168663-
dc.description.abstractIron-catalyzed reactions are receiving a surge of interest owing to the natural abundance and biocompatibility of Fe and the urge to develop practically useful sustainable catalysis for fine chemical industries. This article is a brief account of our studies on the C-O and C-N bond formation reactions catalyzed by Fe complexes supported by oligopyridine, macrocyclic tetraaza, and fluorinated porphyrin ligands. The working principle is the in situ generation of reactive Fe=O and Fe=NR intermediates supported by these oxidatively robust N-donor ligands for oxygen atom/nitrogen group transfer and insertion reactions. The catalytic reactions include C-H bond oxidation of saturated hydrocarbons (up to 87 % yield), epoxidation of alkenes (up to 96 % yield), cis-dihydroxylation of alkenes (up to 99 % yield), epoxidation-isomerization (E-I) reaction of aryl alkenes (up to 94 % yield), amination of C-H bonds (up to 95 % yield), aziridination of alkenes (up to 95 % yield), sulfimidation of sulfides (up to 96 % yield), and amide formation from aldehydes (up to 89 % yield). Many of these catalytic reactions feature high regio- and diastereoselectivity and/or high product yields and substrate conversions, and recyclability of the catalyst, demonstrating the applicability of Fe-catalyzed oxidative organic transformation reactions in practical organic synthesis. © 2012 IUPAC.en_US
dc.languageeng-
dc.publisherInternational Union of Pure and Applied Chemistry. The Journal's web site is located at http://www.iupac.org/publications/pac/-
dc.relation.ispartofPure and Applied Chemistry-
dc.rightsCreative Commons: Attribution 3.0 Hong Kong License-
dc.subjectAmidationen_US
dc.subjectAtom/Group Transferen_US
dc.subjectCatalysisen_US
dc.subjectIronen_US
dc.subjectOxidationen_US
dc.titlePractical iron-catalyzed atom/group transfer and insertion reactions-
dc.typeConference_Paper-
dc.identifier.emailChow, TWS: tobys@hku.hk-
dc.identifier.emailChen, GQ: gqchensd@hku.hk-
dc.identifier.emailLiu, Y: lyg100@hku.hk-
dc.identifier.emailZhou, CY: cyzhou@hku.hk-
dc.identifier.emailChe, CM: cmche@hku.hk-
dc.identifier.authorityLiu, Y=rp00749-
dc.identifier.authorityZhou, CY=rp00843-
dc.identifier.authorityChe, CM=rp00670-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.1351/PAC-CON-11-11-08-
dc.identifier.scopuseid_2-s2.0-84864445077en_US
dc.identifier.hkuros205470-
dc.identifier.hkuros217610-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-84864445077&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume84-
dc.identifier.issue8-
dc.identifier.spage1685-
dc.identifier.epage1704-
dc.identifier.isiWOS:000306643000003-
dc.publisher.placeUnited States-
dc.identifier.scopusauthoridWaiShan, T=55325742300en_US
dc.identifier.scopusauthoridChen, GQ=37100986900en_US
dc.identifier.scopusauthoridLiu, Y=8225912600en_US
dc.identifier.scopusauthoridZhou, CY=35742480200en_US
dc.identifier.scopusauthoridChe, CM=7102442791en_US
dc.customcontrol.immutablejt 130830-
dc.customcontrol.immutablesml 150416-

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