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Conference Paper: Practical iron-catalyzed atom/group transfer and insertion reactions
Title | Practical iron-catalyzed atom/group transfer and insertion reactions |
---|---|
Authors | |
Keywords | Amidation Atom/Group Transfer Catalysis Iron Oxidation |
Issue Date | 2012 |
Publisher | International 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? |
Abstract | Iron-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 Identifier | http://hdl.handle.net/10722/168663 |
ISSN | 2023 Impact Factor: 2.0 2023 SCImago Journal Rankings: 0.435 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Chow, TWS | - |
dc.contributor.author | Chen, GQ | - |
dc.contributor.author | Liu, Y | - |
dc.contributor.author | Zhou, CY | - |
dc.contributor.author | Che, CM | - |
dc.date.accessioned | 2012-10-08T03:24:09Z | - |
dc.date.available | 2012-10-08T03:24:09Z | - |
dc.date.issued | 2012 | - |
dc.identifier.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 | - |
dc.identifier.issn | 0033-4545 | - |
dc.identifier.uri | http://hdl.handle.net/10722/168663 | - |
dc.description.abstract | Iron-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.language | eng | - |
dc.publisher | International Union of Pure and Applied Chemistry. The Journal's web site is located at http://www.iupac.org/publications/pac/ | - |
dc.relation.ispartof | Pure and Applied Chemistry | - |
dc.rights | © 2012 IUPAC. The final publication is available at www.degruyter.com | - |
dc.subject | Amidation | en_US |
dc.subject | Atom/Group Transfer | en_US |
dc.subject | Catalysis | en_US |
dc.subject | Iron | en_US |
dc.subject | Oxidation | en_US |
dc.title | Practical iron-catalyzed atom/group transfer and insertion reactions | - |
dc.type | Conference_Paper | - |
dc.identifier.email | Chow, TWS: tobys@hku.hk | - |
dc.identifier.email | Chen, GQ: gqchensd@hku.hk | - |
dc.identifier.email | Liu, Y: lyg100@hku.hk | - |
dc.identifier.email | Zhou, CY: cyzhou@hku.hk | - |
dc.identifier.email | Che, CM: cmche@hku.hk | - |
dc.identifier.authority | Liu, Y=rp00749 | - |
dc.identifier.authority | Zhou, CY=rp00843 | - |
dc.identifier.authority | Che, CM=rp00670 | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.1351/PAC-CON-11-11-08 | - |
dc.identifier.scopus | eid_2-s2.0-84864445077 | en_US |
dc.identifier.hkuros | 205470 | - |
dc.identifier.hkuros | 217610 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-84864445077&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 84 | - |
dc.identifier.issue | 8 | - |
dc.identifier.spage | 1685 | - |
dc.identifier.epage | 1704 | - |
dc.identifier.isi | WOS:000306643000003 | - |
dc.publisher.place | United States | - |
dc.identifier.scopusauthorid | WaiShan, T=55325742300 | en_US |
dc.identifier.scopusauthorid | Chen, GQ=37100986900 | en_US |
dc.identifier.scopusauthorid | Liu, Y=8225912600 | en_US |
dc.identifier.scopusauthorid | Zhou, CY=35742480200 | en_US |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_US |
dc.customcontrol.immutable | jt 130830 | - |
dc.customcontrol.immutable | sml 150416 | - |
dc.identifier.issnl | 0033-4545 | - |