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Article: A silica gel-supported ruthenium complex of 1,4,7-Trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxide

TitleA silica gel-supported ruthenium complex of 1,4,7-Trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxide
Authors
Issue Date2002
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc
Citation
Journal Of Organic Chemistry, 2002, v. 67 n. 22, p. 7716-7723 How to Cite?
AbstractA silica gel-immobilized [(Me 3tacn)Ru III(CF 3 COO) 2(H 2O)]CF 3CO 2 complex (1-SiO 2, Me 3tacn = 1,4,7- trimethyl-1,4,7-triazacyclononane) was prepared by simple impregnation, and the catalyst was characterized by powdered X-ray diffraction, nitrogen adsorption/desorption, Raman, and diffuse reflectance UV-vis spectroscopies. The supported Ru catalyst can effect facile oxidation of alcohols by tert-butyl hydroperoxide (TBHP). Primary and secondary benzyl, allylic, and propargylic alcohols were transformed to their corresponding aldehydes and ketones in excellent yields; no oxidation of the C=C and C≡C bonds was observed for the allylic and propargylic alcohol oxidations. Likewise alkene epoxidation by TBHP can be achieved by 1-SiO 2; cycloalkenes such as norbornene and cyclooctene were oxidized to their exo-epoxides exclusively in excellent yields (>95%). The 1-SiO 2 catalyst can be recycled and reused for consecutive alcohol and alkene oxidations without significant loss of catalytic activity and selectivity; over 9000 turnovers have been attained for the oxidation of 1-phenyl-1-propanol to 1-phenyl-1-propanone. 4-Substituted phenols were oxidized by the "1 + TBHP" protocol to give exclusively ruthenium-catecholate complexes, which were characterized by UV-vis and ESI-MS spectroscopies. No (tert-butyldioxy)cyclohexadienone and other radical coupling/overoxidation products were produced using the "1 + TBHP" protocol. The formation of ruthenium-catecholate is proposed to proceed via ortho-hydroxylation of phenol.
Persistent Identifierhttp://hdl.handle.net/10722/69791
ISSN
2015 Impact Factor: 4.785
2015 SCImago Journal Rankings: 2.095
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorCheung, WHen_HK
dc.contributor.authorYu, WYen_HK
dc.contributor.authorYip, WPen_HK
dc.contributor.authorZhu, NYen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:16:52Z-
dc.date.available2010-09-06T06:16:52Z-
dc.date.issued2002en_HK
dc.identifier.citationJournal Of Organic Chemistry, 2002, v. 67 n. 22, p. 7716-7723en_HK
dc.identifier.issn0022-3263en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69791-
dc.description.abstractA silica gel-immobilized [(Me 3tacn)Ru III(CF 3 COO) 2(H 2O)]CF 3CO 2 complex (1-SiO 2, Me 3tacn = 1,4,7- trimethyl-1,4,7-triazacyclononane) was prepared by simple impregnation, and the catalyst was characterized by powdered X-ray diffraction, nitrogen adsorption/desorption, Raman, and diffuse reflectance UV-vis spectroscopies. The supported Ru catalyst can effect facile oxidation of alcohols by tert-butyl hydroperoxide (TBHP). Primary and secondary benzyl, allylic, and propargylic alcohols were transformed to their corresponding aldehydes and ketones in excellent yields; no oxidation of the C=C and C≡C bonds was observed for the allylic and propargylic alcohol oxidations. Likewise alkene epoxidation by TBHP can be achieved by 1-SiO 2; cycloalkenes such as norbornene and cyclooctene were oxidized to their exo-epoxides exclusively in excellent yields (>95%). The 1-SiO 2 catalyst can be recycled and reused for consecutive alcohol and alkene oxidations without significant loss of catalytic activity and selectivity; over 9000 turnovers have been attained for the oxidation of 1-phenyl-1-propanol to 1-phenyl-1-propanone. 4-Substituted phenols were oxidized by the "1 + TBHP" protocol to give exclusively ruthenium-catecholate complexes, which were characterized by UV-vis and ESI-MS spectroscopies. No (tert-butyldioxy)cyclohexadienone and other radical coupling/overoxidation products were produced using the "1 + TBHP" protocol. The formation of ruthenium-catecholate is proposed to proceed via ortho-hydroxylation of phenol.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.titleA silica gel-supported ruthenium complex of 1,4,7-Trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxideen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=67&issue=22&spage=7716&epage=7723&date=2002&atitle=A+silica+gel-supported+ruthenium+complex+of+1,4,7-trimethyl-1,4,7-triazacyclononane+as+recyclable+catalyst+for+chemoselective+oxidation+of+alcohols+and+alkenes+by+tert-butyl+hydroperoxideen_HK
dc.identifier.emailCheung, WH: sunnycwh@hku.hken_HK
dc.identifier.emailZhu, NY: nzhu@hkucc.hku.hken_HK
dc.identifier.emailChe, CM: cmche@hku.hken_HK
dc.identifier.authorityCheung, WH=rp00246en_HK
dc.identifier.authorityZhu, NY=rp00845en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo0204404en_HK
dc.identifier.scopuseid_2-s2.0-0036827711en_HK
dc.identifier.hkuros83808en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-0036827711&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume67en_HK
dc.identifier.issue22en_HK
dc.identifier.spage7716en_HK
dc.identifier.epage7723en_HK
dc.identifier.isiWOS:000178820200019-
dc.publisher.placeUnited Statesen_HK
dc.identifier.scopusauthoridCheung, WH=36152058800en_HK
dc.identifier.scopusauthoridYu, WY=7403913673en_HK
dc.identifier.scopusauthoridYip, WP=8751048200en_HK
dc.identifier.scopusauthoridZhu, NY=7201449530en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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