DC Field | Value | Language |
---|---|---|
dc.contributor.author | Ryu, Ho | ko |
dc.contributor.author | Pudasaini, Bimal | ko |
dc.contributor.author | Cho, Dasol | ko |
dc.contributor.author | Hong, Sungwoo | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.date.accessioned | 2022-09-22T08:00:14Z | - |
dc.date.available | 2022-09-22T08:00:14Z | - |
dc.date.created | 2022-09-14 | - |
dc.date.created | 2022-09-14 | - |
dc.date.created | 2022-09-14 | - |
dc.date.issued | 2022-08 | - |
dc.identifier.citation | CHEMICAL SCIENCE, v.13, no.36, pp.10707 - 10714 | - |
dc.identifier.issn | 2041-6520 | - |
dc.identifier.uri | http://hdl.handle.net/10203/298679 | - |
dc.description.abstract | A typical synthetic protocol for preparing 7-azaindoles involves the coupling of 2-aminopyridine and alkyne substrates using a Rh(iii)-catalyst. The catalysis requires the assistance of an external Ag+ oxidant that is thought to regenerate the catalyst and increase the turnover efficiency. Density functional theory (DFT) simulations confirm that Ag+ can oxidize various neutral Rh(iii) intermediates encountered at different stages of the catalysis. Among them, the catalytically relevant species is a cationic Rh(iii)-pyridyl(+) complex (2A), which undergoes C-H activation of pyridine and couples an internal alkyne substrate into the pyridyl ligand to form the desired 7-azaindole product. Computations reveal that the oxidation also accelerates the reaction steps, including C-H activation via concerted metalation deprotonation (CMD), 1,2-alkyne insertion, and reductive elimination, thus highlighting the role of Ag+ as a catalytic promoter for the oxidatively induced reactivity of the Rh-catalyst in 7-azaindole synthesis. DFT calculations show that the catalysis is inefficient without invoking an oxidatively induced reaction pathway. | - |
dc.language | English | - |
dc.publisher | ROYAL SOC CHEMISTRY | - |
dc.title | Oxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive | - |
dc.type | Article | - |
dc.identifier.wosid | 000847734300001 | - |
dc.identifier.scopusid | 2-s2.0-85138634104 | - |
dc.type.rims | ART | - |
dc.citation.volume | 13 | - |
dc.citation.issue | 36 | - |
dc.citation.beginningpage | 10707 | - |
dc.citation.endingpage | 10714 | - |
dc.citation.publicationname | CHEMICAL SCIENCE | - |
dc.identifier.doi | 10.1039/d2sc01650h | - |
dc.contributor.localauthor | Hong, Sungwoo | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Pudasaini, Bimal | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | EFFECTIVE CORE POTENTIALS | - |
dc.subject.keywordPlus | SOLVATION FREE-ENERGIES | - |
dc.subject.keywordPlus | MOLECULAR CALCULATIONS | - |
dc.subject.keywordPlus | DESIGN | - |
dc.subject.keywordPlus | FUNCTIONALIZATION | - |
dc.subject.keywordPlus | INDOLES | - |
dc.subject.keywordPlus | ANALOGS | - |
dc.subject.keywordPlus | AGENTS | - |
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