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Article: Stoichiornetric and catalytic oxidations of alkanes and alcohols mediated by highly oxidizing ruthenium-oxo complexes bearing 6,6'-dichloro-2,2'-bipyridine
Title | Stoichiornetric and catalytic oxidations of alkanes and alcohols mediated by highly oxidizing ruthenium-oxo complexes bearing 6,6'-dichloro-2,2'-bipyridine |
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Authors | |
Issue Date | 2000 |
Publisher | American 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. 7996-8000 How to Cite? |
Abstract | The ruthenium(II) complex cis-[Ru(6,6'-Cl 2bpy) 2(OH 2) 2](CF 3SO 3) 2 (1) is a robust catalyst for C-H bond oxidations of hydrocarbons, including linear alkanes, using tert-butyl hydroperoxide (TBHP) as terminal oxidant. Alcohols can be oxidized by the '1 + TBHP' protocol to the corresponding aldehydes/ketones with high product yields at ambient temperature. Oxidation of 1 with Ce(IV) in aqueous solution affords cis-[Ru(VI)(6,6'-Cl 2bpy) 2O 2] 2+, which is isolated as a green/yellow perchlorate salt (2). Complex 2 is a powerful stoichiometric oxidant for cycloalkane oxidations under mild conditions. Oxidation of cis-decalin is highly stereoretentive; cis-decalinol is obtained in high yield, and formation of trans-decalinol is not observed. Mechanistic studies showing a large primary kinetic isotope effect suggest a hydrogen-atom abstraction pathway. The relative reactivities of cycloalkanes toward oxidation by 2 have been examined through competitive experiments, and comparisons with Gif-type processes are presented. |
Persistent Identifier | http://hdl.handle.net/10722/167661 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
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dc.contributor.author | Che, CM | en_US |
dc.contributor.author | Cheng, KW | en_US |
dc.contributor.author | Chan, MCW | en_US |
dc.contributor.author | Lau, TC | en_US |
dc.contributor.author | Mak, CK | en_US |
dc.date.accessioned | 2012-10-08T03:09:34Z | - |
dc.date.available | 2012-10-08T03:09:34Z | - |
dc.date.issued | 2000 | en_US |
dc.identifier.citation | Journal Of Organic Chemistry, 2000, v. 65 n. 23, p. 7996-8000 | en_US |
dc.identifier.issn | 0022-3263 | en_US |
dc.identifier.uri | http://hdl.handle.net/10722/167661 | - |
dc.description.abstract | The ruthenium(II) complex cis-[Ru(6,6'-Cl 2bpy) 2(OH 2) 2](CF 3SO 3) 2 (1) is a robust catalyst for C-H bond oxidations of hydrocarbons, including linear alkanes, using tert-butyl hydroperoxide (TBHP) as terminal oxidant. Alcohols can be oxidized by the '1 + TBHP' protocol to the corresponding aldehydes/ketones with high product yields at ambient temperature. Oxidation of 1 with Ce(IV) in aqueous solution affords cis-[Ru(VI)(6,6'-Cl 2bpy) 2O 2] 2+, which is isolated as a green/yellow perchlorate salt (2). Complex 2 is a powerful stoichiometric oxidant for cycloalkane oxidations under mild conditions. Oxidation of cis-decalin is highly stereoretentive; cis-decalinol is obtained in high yield, and formation of trans-decalinol is not observed. Mechanistic studies showing a large primary kinetic isotope effect suggest a hydrogen-atom abstraction pathway. The relative reactivities of cycloalkanes toward oxidation by 2 have been examined through competitive experiments, and comparisons with Gif-type processes are presented. | en_US |
dc.language | eng | en_US |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | en_US |
dc.relation.ispartof | Journal of Organic Chemistry | en_US |
dc.title | Stoichiornetric and catalytic oxidations of alkanes and alcohols mediated by highly oxidizing ruthenium-oxo complexes bearing 6,6'-dichloro-2,2'-bipyridine | en_US |
dc.type | Article | en_US |
dc.identifier.email | Che, CM:cmche@hku.hk | en_US |
dc.identifier.authority | Che, CM=rp00670 | en_US |
dc.description.nature | link_to_subscribed_fulltext | en_US |
dc.identifier.doi | 10.1021/jo0010126 | en_US |
dc.identifier.scopus | eid_2-s2.0-0034680620 | en_US |
dc.identifier.hkuros | 59513 | - |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0034680620&selection=ref&src=s&origin=recordpage | en_US |
dc.identifier.volume | 65 | en_US |
dc.identifier.issue | 23 | en_US |
dc.identifier.spage | 7996 | en_US |
dc.identifier.epage | 8000 | en_US |
dc.identifier.isi | WOS:000165491300040 | - |
dc.publisher.place | United States | en_US |
dc.identifier.scopusauthorid | Che, CM=7102442791 | en_US |
dc.identifier.scopusauthorid | Cheng, KW=36439221300 | en_US |
dc.identifier.scopusauthorid | Chan, MCW=7402598116 | en_US |
dc.identifier.scopusauthorid | Lau, TC=7102222310 | en_US |
dc.identifier.scopusauthorid | Mak, CK=7102876260 | en_US |
dc.identifier.issnl | 0022-3263 | - |