ICCAS OpenIR
Ruthenium-Catalyzed Nucleophilic Allylic Substitution Reactions from beta-Silylated Allylic Carbonates
Zhang, Hui-Jun1,2; Demerseman, Bernard2; Toupet, Loic2; Xi, Zhenfeng1; Bruneau, Christian2
2009-09-14
Source PublicationORGANOMETALLICS
ISSN0276-7333
Volume28Issue:17Pages:5173-5182
AbstractThe trans addition of HSiEt(3) to propargylic ethyl carbonates catalyzed by the ruthenium complex [Ru(C(5)Me(5))(MeCN)(3)][PF(6)], 1, leads to H(2)C=C(SiEt(3))CH(R)OCO(2)Et (R = H, Me, Pr(n), or Ph) derivatives as allylic substrates for Subsequent ruthenium-catalyzed nucleophilic allylic Substitution reactions. Ruthenium catalysts based on a [Ru(C(5)Me(5))(2-quinolinecarboxylato)] or [Ru(C(5)Me(5))(2,2'-bipyridine)](+) fragment are more efficient than 1 for access to various H(2)C=C(SiEt(3))CH(R)Nufunctionalized vinylsilanes (R = H, Me; NuH = secondary amine, phenol, dimethylmalonate, methanol). New [Ru(C(5)Me(5))(2-quinolinecarboxylato)(eta(3-)allyl)](+) cationic ruthenium(IV) intermediates are characterized, and experiments using a deuteriurn-labelcd allylic carbonate provide evidence for a regioselectivity arising from the presence of the 2-quinolinecarboxylato (N,O)-chelate.
DOI10.1021/om900437m
Indexed BySCI ; IC
Language英语
WOS IDWOS:000269424200036
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:16[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/67854
Collection中国科学院化学研究所
Corresponding AuthorXi, Zhenfeng
Affiliation1.Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China
2.Univ Rennes 1, CNRS, UMR 6226, F-35042 Rennes, France
Recommended Citation
GB/T 7714
Zhang, Hui-Jun,Demerseman, Bernard,Toupet, Loic,et al. Ruthenium-Catalyzed Nucleophilic Allylic Substitution Reactions from beta-Silylated Allylic Carbonates[J]. ORGANOMETALLICS,2009,28(17):5173-5182.
APA Zhang, Hui-Jun,Demerseman, Bernard,Toupet, Loic,Xi, Zhenfeng,&Bruneau, Christian.(2009).Ruthenium-Catalyzed Nucleophilic Allylic Substitution Reactions from beta-Silylated Allylic Carbonates.ORGANOMETALLICS,28(17),5173-5182.
MLA Zhang, Hui-Jun,et al."Ruthenium-Catalyzed Nucleophilic Allylic Substitution Reactions from beta-Silylated Allylic Carbonates".ORGANOMETALLICS 28.17(2009):5173-5182.
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