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Article: Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts

TitleSelective functionalisation of saturated C-H bonds with metalloporphyrin catalysts
Authors
Issue Date2011
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/Publishing/Journals/cs/index.asp
Citation
Chemical Society Reviews, 2011, v. 40 n. 4, p. 1950-1975 How to Cite?
AbstractThe recent surge of interest in metal-catalysed C-H bond functionalisation reactions reflects the importance of such reactions in biomimetic studies and organic synthesis. This critical review focuses on metalloporphyrin-catalysed saturated C-H bond functionalisation reported since the year 2000, including C-O, C-N and C-C bond formation via hydroxylation, amination and carbenoid insertion, respectively, together with a brief description of previous achievements in this area. Among the metalloporphyrin-catalysed reactions highlighted herein are the hydroxylation of steroids, cycloalkanes and benzylic hydrocarbons; intermolecular amination of steroids, cycloalkanes and benzylic or allylic hydrocarbons; intramolecular amination of sulfamate esters and organic azides; intermolecular carbenoid insertion into benzylic, allylic or alkane C-H bonds; and intramolecular carbenoid C-H insertion of tosylhydrazones. These metalloporphyrin-catalysed saturated C-H bond functionalisation reactions feature high regio-, diastereo- or enantioselectivity and/or high product turnover numbers. Mechanistic studies suggest the involvement of metal-oxo, -imido (or nitrene), and -carbene porphyrin complexes in the reactions. The reactivity of such metal-ligand multiple bonded species towards saturated C-H bonds, including mechanistic studies through both experimental and theoretical means, is also discussed (244 references). © 2011 The Royal Society of Chemistry.
Persistent Identifierhttp://hdl.handle.net/10722/134369
ISSN
2015 Impact Factor: 34.09
2015 SCImago Journal Rankings: 15.228
ISI Accession Number ID
Funding AgencyGrant Number
University of Hong Kong
Hong Kong Research Grants CouncilHKU 1/CRF/08
HKU 7007/08P
University Grants Committee of the Hong Kong SAR of ChinaAoE/P-10/01
Funding Information:

We thank The University of Hong Kong, the Hong Kong Research Grants Council (HKU 1/CRF/08, HKU 7007/08P), and the University Grants Committee of the Hong Kong SAR of China (Area of Excellence Scheme, AoE/P-10/01) for financial support.

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorChe, CMen_HK
dc.contributor.authorLo, VKYen_HK
dc.contributor.authorZhou, CYen_HK
dc.contributor.authorHuang, JSen_HK
dc.date.accessioned2011-06-17T09:18:42Z-
dc.date.available2011-06-17T09:18:42Z-
dc.date.issued2011en_HK
dc.identifier.citationChemical Society Reviews, 2011, v. 40 n. 4, p. 1950-1975en_HK
dc.identifier.issn0306-0012en_HK
dc.identifier.urihttp://hdl.handle.net/10722/134369-
dc.description.abstractThe recent surge of interest in metal-catalysed C-H bond functionalisation reactions reflects the importance of such reactions in biomimetic studies and organic synthesis. This critical review focuses on metalloporphyrin-catalysed saturated C-H bond functionalisation reported since the year 2000, including C-O, C-N and C-C bond formation via hydroxylation, amination and carbenoid insertion, respectively, together with a brief description of previous achievements in this area. Among the metalloporphyrin-catalysed reactions highlighted herein are the hydroxylation of steroids, cycloalkanes and benzylic hydrocarbons; intermolecular amination of steroids, cycloalkanes and benzylic or allylic hydrocarbons; intramolecular amination of sulfamate esters and organic azides; intermolecular carbenoid insertion into benzylic, allylic or alkane C-H bonds; and intramolecular carbenoid C-H insertion of tosylhydrazones. These metalloporphyrin-catalysed saturated C-H bond functionalisation reactions feature high regio-, diastereo- or enantioselectivity and/or high product turnover numbers. Mechanistic studies suggest the involvement of metal-oxo, -imido (or nitrene), and -carbene porphyrin complexes in the reactions. The reactivity of such metal-ligand multiple bonded species towards saturated C-H bonds, including mechanistic studies through both experimental and theoretical means, is also discussed (244 references). © 2011 The Royal Society of Chemistry.en_HK
dc.languageengen_US
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/Publishing/Journals/cs/index.aspen_HK
dc.relation.ispartofChemical Society Reviewsen_HK
dc.subject.meshAmination-
dc.subject.meshCarbon - chemistry-
dc.subject.meshCatalysis-
dc.subject.meshHydrogen - chemistry-
dc.subject.meshMetalloporphyrins - chemistry-
dc.titleSelective functionalisation of saturated C-H bonds with metalloporphyrin catalystsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0306-0012&volume=40&issue=4&spage=1950&epage=1975&date=2011&atitle=Selective+functionalisation+of+saturated+C–H+Bonds+with+metalloporphyrin+catalysts-
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.emailZhou, CY:cyzhou@hku.hken_HK
dc.identifier.emailHuang, JS:jshuang@hkucc.hku.hken_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.identifier.authorityZhou, CY=rp00843en_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/c0cs00142ben_HK
dc.identifier.pmid21387046-
dc.identifier.scopuseid_2-s2.0-79959790191en_HK
dc.identifier.hkuros185778en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-79959790191&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume40en_HK
dc.identifier.issue4en_HK
dc.identifier.spage1950en_HK
dc.identifier.epage1975en_HK
dc.identifier.isiWOS:000288609400010-
dc.publisher.placeUnited Kingdomen_HK
dc.relation.projectInstitute of molecular technology for drug discovery and synthesis-
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridLo, VKY=13406071200en_HK
dc.identifier.scopusauthoridZhou, CY=35742480200en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK

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