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Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes
dc.creator | Aleksić, Jovana | |
dc.creator | Stojanović, Milovan | |
dc.creator | Baranac-Stojanović, Marija | |
dc.date.accessioned | 2019-10-11T21:56:12Z | |
dc.date.available | 2019-05-14 | |
dc.date.issued | 2018 | |
dc.identifier.issn | 1861-4728 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/3135 | |
dc.description.abstract | We 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.publisher | Wiley-V C H Verlag Gmbh, Weinheim | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172020/RS// | |
dc.relation | info:eu-repo/grantAgreement/EC/FP7/256716/EU// | |
dc.rights | embargoedAccess | |
dc.source | Chemistry-An Asian Journal | |
dc.subject | amines | en |
dc.subject | conjugation | en |
dc.subject | green chemistry | en |
dc.subject | Michael addition | en |
dc.subject | propiolic esters | en |
dc.title | Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Стојановић, Милован; Aлексић, Јована; Баранац-Стојановић, Марија; | |
dc.citation.volume | 13 | |
dc.citation.issue | 14 | |
dc.citation.spage | 1811 | |
dc.citation.epage | 1835 | |
dc.citation.other | 13(14): 1811-1835 | |
dc.citation.rank | M21 | |
dc.description.other | This is the peer-reviewed version of the following article: Aleksić, J.; Stojanović, M.; Baranac-Stojanović, M. Silica Gel as a Promoter of Sequential Aza-Michael/Michael Reactions of Amines and Propiolic Esters: Solvent- and Metal-Free Synthesis of Polyfunctionalized Conjugated Dienes. Chemistry - An Asian Journal 2018, 13 (14), 1811–1835. [https://doi.org/10.1002/asia.201800645] | |
dc.description.other | [http://cer.ihtm.bg.ac.rs/handle/123456789/2451] | |
dc.identifier.pmid | 29757499 | |
dc.identifier.doi | 10.1002/asia.201800645 | |
dc.identifier.fulltext | https://cer.ihtm.bg.ac.rs/bitstream/id/14133/asia.201800645.pdf | |
dc.identifier.scopus | 2-s2.0-85050126437 | |
dc.identifier.wos | 000439497300008 | |
dc.type.version | acceptedVersion |