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Article: Amidation of unfunctionalized hydrocarbons catalyzed by ruthenium cyclic amine or bipyridine complexes

TitleAmidation of unfunctionalized hydrocarbons catalyzed by ruthenium cyclic amine or bipyridine complexes
Authors
Issue Date2000
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2000, v. 65 n. 23, p. 7858-7864 How to Cite?
AbstractSelective amidation of simple hydrocarbons with pre-isolated and in-situ formed iminoiodanes catalyzed by ruthenium complexes [Ru(III)(Me 3tacn)(CF 3CO 2) 3·H 2O] (2b, Me 3tacn = N,N',N -trimethyl-1,4,7-triazacyclononane) and cis-[Ru(II)(6,6'-Cl 2bpy) 2Cl 2] (3, 6,6'-Cl 2bpy = 6,6'-dichloro-2,2'-bipyridine) was investigated. With PhI=NTs as nitrogen source, both catalysts efficiently promote the amidation of adamantane, cyclohexene, ethylbenzene, cumene, indan, tetralin, and diphenylmethane to afford N-substituted sulfonamides in 80-93% yields with high selectivity. Competitive amidations of para-substituted ethylbenzenes and kinetic isotope effect for the amidation of cyclohexene/cyclohexene-d 10 suggest that the amidation processes probably proceed via the hydrogen abstraction by a reactive Ru=NTs species to form a carboradical intermediate. The amidation with PhI(OAc) 2/TsNH 2 gave results comparable to those obtained with PhI=NTs. Extension of the 'PhI(OAc) 2/TsNH 2 + catalyst 2b or 3' protocol to MeSO 2NH 2 and PhCONH 2 with ethylbenzene as substrate produced the corresponding N-substituted amides in up to 89% yield.
Persistent Identifierhttp://hdl.handle.net/10722/68758
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorAu, SMen_HK
dc.contributor.authorHuang, JSen_HK
dc.contributor.authorChe, CMen_HK
dc.contributor.authorYu, WYen_HK
dc.date.accessioned2010-09-06T06:07:27Z-
dc.date.available2010-09-06T06:07:27Z-
dc.date.issued2000en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2000, v. 65 n. 23, p. 7858-7864en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/68758-
dc.description.abstractSelective amidation of simple hydrocarbons with pre-isolated and in-situ formed iminoiodanes catalyzed by ruthenium complexes [Ru(III)(Me 3tacn)(CF 3CO 2) 3·H 2O] (2b, Me 3tacn = N,N',N -trimethyl-1,4,7-triazacyclononane) and cis-[Ru(II)(6,6'-Cl 2bpy) 2Cl 2] (3, 6,6'-Cl 2bpy = 6,6'-dichloro-2,2'-bipyridine) was investigated. With PhI=NTs as nitrogen source, both catalysts efficiently promote the amidation of adamantane, cyclohexene, ethylbenzene, cumene, indan, tetralin, and diphenylmethane to afford N-substituted sulfonamides in 80-93% yields with high selectivity. Competitive amidations of para-substituted ethylbenzenes and kinetic isotope effect for the amidation of cyclohexene/cyclohexene-d 10 suggest that the amidation processes probably proceed via the hydrogen abstraction by a reactive Ru=NTs species to form a carboradical intermediate. The amidation with PhI(OAc) 2/TsNH 2 gave results comparable to those obtained with PhI=NTs. Extension of the 'PhI(OAc) 2/TsNH 2 + catalyst 2b or 3' protocol to MeSO 2NH 2 and PhCONH 2 with ethylbenzene as substrate produced the corresponding N-substituted amides in up to 89% yield.en_HK
dc.languageengen_HK
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jocen_HK
dc.relation.ispartofJournal of Organic Chemistryen_HK
dc.titleAmidation of unfunctionalized hydrocarbons catalyzed by ruthenium cyclic amine or bipyridine complexesen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=65&issue=23&spage=7858&epage=7864&date=2000&atitle=Amidation+of+unfunctionalized+hydrocarbons+catalyzed+by+ruthenium+cyclic+amine+or+bipyridine+complexesen_HK
dc.identifier.emailHuang, JS:jshuang@hkucc.hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityHuang, JS=rp00709en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo000881sen_HK
dc.identifier.scopuseid_2-s2.0-0034680660en_HK
dc.identifier.hkuros56708en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0034680660&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume65en_HK
dc.identifier.issue23en_HK
dc.identifier.spage7858en_HK
dc.identifier.epage7864en_HK
dc.identifier.isiWOS:000165491300022-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridAu, SM=7005457811en_HK
dc.identifier.scopusauthoridHuang, JS=7407192639en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK
dc.identifier.scopusauthoridYu, WY=7403913673en_HK

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