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dc.creatorAleksić, Jovana
dc.creatorStojanović, Milovan
dc.creatorBaranac-Stojanović, Marija
dc.date.accessioned2019-01-30T18:00:44Z
dc.date.available2019-01-30T18:00:44Z
dc.date.issued2018
dc.identifier.issn1861-4728
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/2451
dc.description.abstractWe present an efficient, simple, metal- and solvent-free silica-gel-promoted synthesis of functionalized conjugated dienes by sequential aza-Michael/Michael reactions by starting from commercially available primary amines and propiolic esters. The scope and usefulness of the method is demonstrated for 31examples, including a range of propiolic esters, aliphatic amines, and differently substituted aromatic amines. For aliphatic amines, the products were obtained within 0.5 to 4h in 52 to 85% yield, compared with 3.5 to 22h under classical solution-phase synthesis, which proceeds with similar or lower yields. The method was found to be particularly useful for weakly nucleophilic aromatic amines, which provided products in 21 to 73% yield over 2.5 to 9.5h compared with yields of 0 to 49% over 1 to 6d under standard solution-phase conditions, and for more hydrophobic esters that gave products in yields of 47 to 79% over 1 to 3h compared with 0 to 45% over 4 to 114h in solvent.en
dc.publisherWiley-V C H Verlag Gmbh, Weinheim
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172020/RS//
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/256716/EU//
dc.rightsrestrictedAccess
dc.sourceChemistry-An Asian Journal
dc.subjectaminesen
dc.subjectconjugationen
dc.subjectgreen chemistryen
dc.subjectMichael additionen
dc.subjectpropiolic estersen
dc.titleSilica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienesen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractAлексић, Јована; Баранац-Стојановиц, Марија; Стојановић, Милован;
dc.citation.volume13
dc.citation.issue14
dc.citation.spage1811
dc.citation.epage1835
dc.citation.other13(14): 1811-1835
dc.citation.rankM21
dc.description.otherThe peer-reviewed version: [http://cer.ihtm.bg.ac.rs/handle/123456789/3135]
dc.identifier.pmid29757499
dc.identifier.doi10.1002/asia.201800645
dc.identifier.rcubConv_3970
dc.identifier.scopus2-s2.0-85050126437
dc.identifier.wos000439497300008
dc.type.versionpublishedVersion


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