Palladium-Catalyzed Divergent Arylation of Triazolopyridines: A Computational Study
DC Field | Value | Language |
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dc.contributor.author | Deyaa I. AbuSalim | - |
dc.contributor.author | Sungwoo Hong | - |
dc.contributor.author | Mu-Hyun Baik | - |
dc.date.available | 2018-12-13T10:45:33Z | - |
dc.date.created | 2018-09-17 | - |
dc.date.issued | 2018-09 | - |
dc.identifier.issn | 1861-4728 | - |
dc.identifier.uri | https://pr.ibs.re.kr/handle/8788114/4921 | - |
dc.description.abstract | The mechanisms for new palladium-catalyzed divergent reactions of triazolopyridines were investigated by means of DFT calculations. Previously, it was observed experimentally that cross-coupling at the C7-position of triazolopyridines occurred when a strong base was used, whereas the reaction could be diverted to the C3-position if a weak base was employed. Calculations suggest that a strong base, such as tert-butoxide, can easily deprotonate C7−H, independent of the palladium metal, and deliver the preactivated substrate to palladium, which can reductively eliminate the final product. Without a strong base, the palladium(II) center reacts with the ring-opened diazo imine isomer of triazolopyridine to initially form a palladium(II)–carbene intermediate, which undergoes migratory insertion followed by β-hydride elimination to afford a 1,1-disubstituted alkene. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinhei | - |
dc.description.uri | 1 | - |
dc.language | 영어 | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.subject | arylation | - |
dc.subject | carbenes | - |
dc.subject | density functional calculations | - |
dc.subject | palladium | - |
dc.subject | reaction mechanisms | - |
dc.title | Palladium-Catalyzed Divergent Arylation of Triazolopyridines: A Computational Study | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.identifier.wosid | 000443679400044 | - |
dc.identifier.scopusid | 2-s2.0-85052701208 | - |
dc.identifier.rimsid | 65481 | - |
dc.contributor.affiliatedAuthor | Deyaa I. AbuSalim | - |
dc.contributor.affiliatedAuthor | Sungwoo Hong | - |
dc.contributor.affiliatedAuthor | Mu-Hyun Baik | - |
dc.identifier.doi | 10.1002/asia.201800498 | - |
dc.identifier.bibliographicCitation | CHEMISTRY-AN ASIAN JOURNAL, v.13, no.17, pp.2505 - 2510 | - |
dc.citation.title | CHEMISTRY-AN ASIAN JOURNAL | - |
dc.citation.volume | 13 | - |
dc.citation.number | 17 | - |
dc.citation.startPage | 2505 | - |
dc.citation.endPage | 2510 | - |
dc.embargo.liftdate | 9999-12-31 | - |
dc.embargo.terms | 9999-12-31 | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.subject.keywordAuthor | arylation | - |
dc.subject.keywordAuthor | carbenes | - |
dc.subject.keywordAuthor | density functional calculations | - |
dc.subject.keywordAuthor | palladium | - |
dc.subject.keywordAuthor | reaction mechanisms | - |