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dc.creatorNikolić, Andrea
dc.creatorStanić, Jelena
dc.creatorZlatar, Matija
dc.creatorGruden, Maja
dc.creatorAnđelković, Boban
dc.creatorSelaković, Života
dc.creatorAjdačić, Vladimir
dc.creatorOpsenica, Igor
dc.date.accessioned2021-04-16T08:47:31Z
dc.date.available2021-04-16T08:47:31Z
dc.date.issued2021
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttps://cherry.chem.bg.ac.rs/handle/123456789/4358
dc.description.abstractThe Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
dc.publisherAmerican Chemical Society (ACS)en
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200168/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200288/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200026/RS//
dc.relationSerbian Academy of Sciences and Arts (01-2019-F65)
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/256716/EU//
dc.relation.isversionofhttps://cherry.chem.bg.ac.rs/handle/123456789/4359
dc.relation.isreferencedbyhttps://cherry.chem.bg.ac.rs/handle/123456789/4360
dc.rightsrestrictedAccess
dc.sourceThe Journal of Organic Chemistryen
dc.subjectPd-catalyzed N-arylation
dc.subjectsynthesis
dc.subjecttetrazoles
dc.subjectDFT
dc.subjectmechanism
dc.subjectDimroth rearrangement
dc.subjectstability
dc.subjectNMR analysis
dc.subjectthermodynamical control
dc.subjectreactions
dc.subjectequilibrium
dc.subjectrate-determining step
dc.subjectisomers
dc.titleControlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-aminesen
dc.typearticleen
dc.rights.licenseARR
dcterms.abstractОпсеница, Игор; Селаковић, Живота; Aјдачић, Владимир; Станић, Јелена; Николић, Aндреа; Златар, Матија; Груден, Маја; Aнђелковић, Бобан;
dc.citation.volume86
dc.citation.issue6
dc.citation.spage4794
dc.citation.epage4803
dc.identifier.wos000631442900036
dc.identifier.doi10.1021/acs.joc.1c00282
dc.citation.rankM21~
dc.identifier.pmid33683905
dc.description.otherThe peer-reviewed version: [https://cherry.chem.bg.ac.rs/handle/123456789/4359]
dc.description.otherSupplementary data: [https://cherry.chem.bg.ac.rs/handle/123456789/4360]
dc.type.versionpublishedVersion
dc.identifier.scopus2-s2.0-85103457952


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