A Study of Palladium Catalyzed Intra/Intermolecular Cascade Cross Coupling/Cyclizations Involving Bicyclopropylidene

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dc.contributor.authorDemircan, Aydin
dc.date.accessioned2019-08-01T13:38:39Z
dc.date.available2019-08-01T13:38:39Z
dc.date.issued2014
dc.departmentNiğde ÖHÜ
dc.description.abstractThe compounds [3-(2-Bromocyclohex-2-enyloxy) prop-1-ynyl]-tert-butyldimethylsilane 3, [4-(2-bromocyclohex-2-en-1-yloxy)but-2-yn-1-yloxy] tert-butyldimethylsilane 5 and dimethyl 2-(2-bromocyclohex-2-enyl)-2-(3-(tert-butyldimethylsilanyl) prop-2ynyl) malonate 9 were prepared and subjected to palladium-catalyzed intra-intermolecular cascade cross couplings incorporating bicyclopropylidene 10 under two types of conditions. In the presence of Pd(OAc)(2), PPh3 and K2CO3 in acetonitrile at 80 degrees C, the products were indene analogues, cross-conjugated tetraenes 11, 12 and 13, respectively. The corresponding spirocyclopropanated tricycle 16 in dimethylformamide at 110 degrees C was obtained, albeit in low yield (24%), and observed as an equimolar mixture of diastereomers, whereas 14, 15 were not fully isolated.
dc.description.sponsorshipThe Scientific and Technological Research Council of Turkey [TUBITAK-2219]; TUBITAK
dc.description.sponsorshipAuthor would like to thank to Armin de Meijere all for his support and proofreading. This work was also supported by The Scientific and Technological Research Council of Turkey (TUBITAK-2219). A. D. is indebted to TUBITAK for a travel grant and research fellowship to perform some experimental work in the laboratory of Armin de Meijere at the Georg-August-Universitat Gottingen, Germany.
dc.identifier.doi10.3390/molecules19056058
dc.identifier.endpage6069
dc.identifier.issn1420-3049
dc.identifier.issue5
dc.identifier.pmid24828378
dc.identifier.scopus2-s2.0-84901392065
dc.identifier.scopusqualityQ1
dc.identifier.startpage6058
dc.identifier.urihttps://dx.doi.org/10.3390/molecules19056058
dc.identifier.urihttps://hdl.handle.net/11480/4172
dc.identifier.volume19
dc.identifier.wosWOS:000337113000038
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorDemircan, Aydin
dc.language.isoen
dc.publisherMDPI AG
dc.relation.ispartofMOLECULES
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectcascade reactions
dc.subjectcross-coupling
dc.subjectpalladium
dc.subjectcyclopropanes
dc.subjectelectrocyclization
dc.titleA Study of Palladium Catalyzed Intra/Intermolecular Cascade Cross Coupling/Cyclizations Involving Bicyclopropylidene
dc.typeArticle

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