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Article: [FeIII(F20-tpp)Cl] Is an effective catalyst for nitrene transfer reactions and animation of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions

Title[FeIII(F20-tpp)Cl] Is an effective catalyst for nitrene transfer reactions and animation of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditions
Authors
KeywordsAllylic compounds
Azides
C-h activation
Microwave chemistry
Porphyrinoids
Issue Date2010
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2010, v. 16 n. 34, p. 10494-10501 How to Cite?
Abstract[FeIII(F20-tpp)Cl] (F20tpp = meso- tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95% yields), sulfimidation of sulfides (11 examples, 76-96% yields), allylic amidation/amination of α-methylstyrenes (15 examples, 68-83% yields), and amination of saturated C-H bonds including that of cycloalkanes and adamantane (eight examples, 64-80% yields) can be accomplished by using 2 mol % [FeIII(F20- tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C-H bonds (three examples) can be reduced by up to 16fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA. Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/134380
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
Funding AgencyGrant Number
Hong Kong Research Grants CouncilHKU1/CRF/08
HKU700708
Areas of Excellence Scheme under the University Grants Committee of the Hong Kong Special Administrative Region, ChinaAoE/P-10/01
Funding Information:

This work was supported by the Hong Kong Research Grants Council (HKU1/CRF/08 and HKU700708) and the Areas of Excellence Scheme established under the University Grants Committee of the Hong Kong Special Administrative Region, China (AoE/P-10/01).

References
Grants

 

DC FieldValueLanguage
dc.contributor.authorLiu, Yen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2011-06-17T09:18:49Z-
dc.date.available2011-06-17T09:18:49Z-
dc.date.issued2010en_HK
dc.identifier.citationChemistry - A European Journal, 2010, v. 16 n. 34, p. 10494-10501en_HK
dc.identifier.issn0947-6539en_HK
dc.identifier.urihttp://hdl.handle.net/10722/134380-
dc.description.abstract[FeIII(F20-tpp)Cl] (F20tpp = meso- tetrakis(pentafluorophenyl)porphyrinato dianion) is an effective catalyst for imido/nitrene insertion reactions using sulfonyl and aryl azides as nitrogen source. Under thermal conditions, aziridination of aryl and alkyl alkenes (16 examples, 60-95% yields), sulfimidation of sulfides (11 examples, 76-96% yields), allylic amidation/amination of α-methylstyrenes (15 examples, 68-83% yields), and amination of saturated C-H bonds including that of cycloalkanes and adamantane (eight examples, 64-80% yields) can be accomplished by using 2 mol % [FeIII(F20- tpp)Cl] as catalyst. Under microwave irradiation conditions, the reaction time of aziridination (four examples), allylic amination (five examples), sulfimidation (two examples), and amination of saturated C-H bonds (three examples) can be reduced by up to 16fold (24-48 versus 1.5-6 h) without significantly affecting the product yield and substrate conversion. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA. Weinheim.en_HK
dc.languageengen_US
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistryen_HK
dc.relation.ispartofChemistry - A European Journalen_HK
dc.subjectAllylic compoundsen_HK
dc.subjectAzidesen_HK
dc.subjectC-h activationen_HK
dc.subjectMicrowave chemistryen_HK
dc.subjectPorphyrinoidsen_HK
dc.subject.meshAzides - chemistry-
dc.subject.meshHydrocarbons - chemistry-
dc.subject.meshMetalloporphyrins - chemistry-
dc.subject.meshNitrogen - chemistry-
dc.subject.meshSulfhydryl Compounds - chemistry-
dc.title[FeIII(F20-tpp)Cl] Is an effective catalyst for nitrene transfer reactions and animation of saturated hydrocarbons with sulfonyl and aryl azides as nitrogen source under thermal and microwave-assisted conditionsen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0947-6539&volume=16&issue=34&spage=10494&epage=10501&date=2010&atitle=[FeIII(F20-tpp)Cl]+is+an+effective+catalyst+for+nitrene+transfer+reactions+and+animation+of+saturated+hydrocarbons+with+sulfonyl+and+aryl+azides+as+nitrogen+source+under+thermal+and+microwave-assisted+conditions-
dc.identifier.emailLiu, Y:lyg100@hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityLiu, Y=rp00749en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.201000581en_HK
dc.identifier.pmid20648488-
dc.identifier.scopuseid_2-s2.0-77956434740en_HK
dc.identifier.hkuros185819en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-77956434740&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume16en_HK
dc.identifier.issue34en_HK
dc.identifier.spage10494en_HK
dc.identifier.epage10501en_HK
dc.identifier.isiWOS:000282539700028-
dc.publisher.placeGermanyen_HK
dc.relation.projectReactive Metal-Ligand Multiple Bonded Complexes. From Biomimetic Reactions to Highly Efficient Chemical Synthesis-
dc.relation.projectInstitute of molecular technology for drug discovery and synthesis-
dc.identifier.scopusauthoridLiu, Y=8225912600en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.citeulike8218109-

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