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Article: Ruthenium-porphyrin-catalyzed carbenoid transfer reactions

TitleRuthenium-porphyrin-catalyzed carbenoid transfer reactions
Authors
Keywordscarbenoid transfer reactions
catalysis
natural products
porphyrins
ruthenium
Issue Date2010
PublisherGeorg Thieme Verlag. The Journal's web site is located at http://www.thieme-chemistry.com/thieme-chemistry/journals/info/synlett/index.shtml
Citation
Synlett, 2010 n. 18, p. 2681-2700 How to Cite?
AbstractRuthenium-porphyrins are effective catalysts for a wide variety of carbenoid transfer reactions, such as alkene cyclopropanation, carbon-hydrogen, nitrogen-hydrogen, or sulfur-hydrogen (X-H, X = C, N, S) bond insertion, diazo coupling, carbonyl or azomethine ylide formation/1,3-dipolar cycloaddition, and halonium, sulfonium, or ammonium ylide formation/[2,3]-sigmatropic rearrangement reactions. Extensive studies have demonstrated that ruthenium-porphyrins exhibit high stability, high product turnover numbers, and remarkable selectivity in catalytic carbenoid transfer reactions. The catalysis has been successfully applied to the synthesis of organic building blocks and natural products, and to the modification of peptides and proteins. 1 Introduction 2 Catalyst Types 3 Cyclopropanation Reactions 4 Carbon-Hydrogen, Nitrogen-Hydrogen, and Sulfur-Hydrogen Bond Insertion Reactions 5 Alkene Formation Reactions 5.1 Coupling of Diazo Compounds 5.2 Olefination of Aldehydes 6 Ylide Formation and Subsequent Reactions 6.1 Carbonyl Ylide Formation/1,3-Dipolar Cycloaddition 6.2 Azomethine Ylide Formation/1,3-Dipolar Cycloaddition 6.3 Halonium Ylide Formation/[2,3]-Sigmatropic Rearrangement 6.4 Sulfonium or Ammonium Ylide Formation/[2,3]-Sigmatropic Rearrangement 7 Comparison of (Carbene)ruthenium-Porphyrin Complexes with Iron and Osmium Analogues 8 Conclusion. © 2010 Georg Thieme Verlag Stuttgart · New York.
Persistent Identifierhttp://hdl.handle.net/10722/134392
ISSN
2015 Impact Factor: 2.323
2015 SCImago Journal Rankings: 0.908
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 acknowledge support from the University Development Fund of 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).

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorZhou, CYen_HK
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2011-06-17T09:18:57Z-
dc.date.available2011-06-17T09:18:57Z-
dc.date.issued2010en_HK
dc.identifier.citationSynlett, 2010 n. 18, p. 2681-2700en_HK
dc.identifier.issn0936-5214en_HK
dc.identifier.urihttp://hdl.handle.net/10722/134392-
dc.description.abstractRuthenium-porphyrins are effective catalysts for a wide variety of carbenoid transfer reactions, such as alkene cyclopropanation, carbon-hydrogen, nitrogen-hydrogen, or sulfur-hydrogen (X-H, X = C, N, S) bond insertion, diazo coupling, carbonyl or azomethine ylide formation/1,3-dipolar cycloaddition, and halonium, sulfonium, or ammonium ylide formation/[2,3]-sigmatropic rearrangement reactions. Extensive studies have demonstrated that ruthenium-porphyrins exhibit high stability, high product turnover numbers, and remarkable selectivity in catalytic carbenoid transfer reactions. The catalysis has been successfully applied to the synthesis of organic building blocks and natural products, and to the modification of peptides and proteins. 1 Introduction 2 Catalyst Types 3 Cyclopropanation Reactions 4 Carbon-Hydrogen, Nitrogen-Hydrogen, and Sulfur-Hydrogen Bond Insertion Reactions 5 Alkene Formation Reactions 5.1 Coupling of Diazo Compounds 5.2 Olefination of Aldehydes 6 Ylide Formation and Subsequent Reactions 6.1 Carbonyl Ylide Formation/1,3-Dipolar Cycloaddition 6.2 Azomethine Ylide Formation/1,3-Dipolar Cycloaddition 6.3 Halonium Ylide Formation/[2,3]-Sigmatropic Rearrangement 6.4 Sulfonium or Ammonium Ylide Formation/[2,3]-Sigmatropic Rearrangement 7 Comparison of (Carbene)ruthenium-Porphyrin Complexes with Iron and Osmium Analogues 8 Conclusion. © 2010 Georg Thieme Verlag Stuttgart · New York.en_HK
dc.languageengen_US
dc.publisherGeorg Thieme Verlag. The Journal's web site is located at http://www.thieme-chemistry.com/thieme-chemistry/journals/info/synlett/index.shtmlen_HK
dc.relation.ispartofSynletten_HK
dc.rightsSynlett. Copyright © Georg Thieme Verlag.-
dc.subjectcarbenoid transfer reactionsen_HK
dc.subjectcatalysisen_HK
dc.subjectnatural productsen_HK
dc.subjectporphyrinsen_HK
dc.subjectrutheniumen_HK
dc.titleRuthenium-porphyrin-catalyzed carbenoid transfer reactionsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0936-5214&volume=18&spage=2681&epage=2700&date=2010&atitle=Ruthenium-porphyrin-catalyzed+carbenoid+transfer+reactions-
dc.identifier.emailZhou, CY:cyzhou@hku.hken_HK
dc.identifier.emailHuang, JS:jshuang@hkucc.hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityZhou, CY=rp00843en_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_OA_fulltext-
dc.identifier.doi10.1055/s-0030-1259017en_HK
dc.identifier.scopuseid_2-s2.0-78149238614en_HK
dc.identifier.hkuros185858en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-78149238614&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume18en_US
dc.identifier.issue18en_HK
dc.identifier.spage2681en_HK
dc.identifier.epage2700en_HK
dc.identifier.isiWOS:000283747200001-
dc.publisher.placeGermanyen_HK
dc.relation.projectInstitute of molecular technology for drug discovery and synthesis-
dc.identifier.scopusauthoridZhou, CY=35742480200en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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