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Novel [ruthenium(substituted-tetramethylcyclopentadiene) (2-quinolinecarboxylato)(allyl)] hexafluorophosphate complexes as efficient catalysts for highly regioselective nucleophilic substitution of aliphatic allylic substrates
Zhang, Hui-Jun1,2; Demersernan, Bernard2; Toupet, Loiec2; Xi, Zhenfeng1; Bruneau, Christian2
2008-06-01
Source PublicationADVANCED SYNTHESIS & CATALYSIS
ISSN1615-4150
Volume350Issue:10Pages:1601-1609
AbstractStable [ruthenium(R-substituted-tetramethylcyclopentadiene)(2-quinolinecarboxylato)(I-R'- substituted-allyl) hexafluorophosphate (R= Me, R'= H, Me, n-Pr, Ph; R=t-Bu, R'=Me) and [ruthenium(pentamethylcyclopentadiene)(2-quinolinecar- boxylato)(1-n-propylallyl)] tetrafluoroborate (4a), as allylruthenium(IV) complexes, have been synthesized in one step, starting from [ruthenium (R-substituted-tetramethylcyclopentadiene)tris(acetonitrile) hexafluorophosphate or tetrafluoroborate complexes, quinaldic acid, and allylic alcohols. Single stereoisomers are obtained and the X-ray single crystal structure determinations of 3b (R=t-Bu, R'=Me) and 4'a allow one to specify the preferred arrangement. Complexes 3a (R=R'=Me) and 3b are involved as precatalysts favoring the formation of branched products in regioselective nucleophilic allylic substitution reactions, starting from ethyl 2-(E)-hexen-1-yl carbonate and chlorohexene as unsymmetrical aliphatic allylic substrates. Phenols, dimethyl malonate, and primary (aniline) and secondary (pyrrolidine, piperidine) amines have been used as nucleophiles under mild basic conditions. For the first time, the regioselectivity in favor of the branched product obtained from purely aliphatic allylic substrates is close to the high regioselectivity previously reached starting from cinnamyl-type substrates in the presence of ruthenium catalysts.
KeywordAllyl Ligands Allylation Homogeneous Catalysis Regioselectivity Ruthenium
DOI10.1002/adsc.200800135
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000257596700024
PublisherWILEY-BLACKWELL
Citation statistics
Cited Times:35[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/63720
Collection中国科学院化学研究所
Corresponding AuthorXi, Zhenfeng
Affiliation1.Peking Univ, BNLMS, Key Lab Ioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China
2.Univ Rennes 1, CNRS, UMR Sci Chim Rennes 6226, F-35042 Rennes, France
Recommended Citation
GB/T 7714
Zhang, Hui-Jun,Demersernan, Bernard,Toupet, Loiec,et al. Novel [ruthenium(substituted-tetramethylcyclopentadiene) (2-quinolinecarboxylato)(allyl)] hexafluorophosphate complexes as efficient catalysts for highly regioselective nucleophilic substitution of aliphatic allylic substrates[J]. ADVANCED SYNTHESIS & CATALYSIS,2008,350(10):1601-1609.
APA Zhang, Hui-Jun,Demersernan, Bernard,Toupet, Loiec,Xi, Zhenfeng,&Bruneau, Christian.(2008).Novel [ruthenium(substituted-tetramethylcyclopentadiene) (2-quinolinecarboxylato)(allyl)] hexafluorophosphate complexes as efficient catalysts for highly regioselective nucleophilic substitution of aliphatic allylic substrates.ADVANCED SYNTHESIS & CATALYSIS,350(10),1601-1609.
MLA Zhang, Hui-Jun,et al."Novel [ruthenium(substituted-tetramethylcyclopentadiene) (2-quinolinecarboxylato)(allyl)] hexafluorophosphate complexes as efficient catalysts for highly regioselective nucleophilic substitution of aliphatic allylic substrates".ADVANCED SYNTHESIS & CATALYSIS 350.10(2008):1601-1609.
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