Oxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive

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dc.contributor.authorRyu, Hoko
dc.contributor.authorPudasaini, Bimalko
dc.contributor.authorCho, Dasolko
dc.contributor.authorHong, Sungwooko
dc.contributor.authorBaik, Mu-Hyunko
dc.date.accessioned2022-09-22T08:00:14Z-
dc.date.available2022-09-22T08:00:14Z-
dc.date.created2022-09-14-
dc.date.created2022-09-14-
dc.date.created2022-09-14-
dc.date.issued2022-08-
dc.identifier.citationCHEMICAL SCIENCE, v.13, no.36, pp.10707 - 10714-
dc.identifier.issn2041-6520-
dc.identifier.urihttp://hdl.handle.net/10203/298679-
dc.description.abstractA 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.languageEnglish-
dc.publisherROYAL SOC CHEMISTRY-
dc.titleOxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive-
dc.typeArticle-
dc.identifier.wosid000847734300001-
dc.identifier.scopusid2-s2.0-85138634104-
dc.type.rimsART-
dc.citation.volume13-
dc.citation.issue36-
dc.citation.beginningpage10707-
dc.citation.endingpage10714-
dc.citation.publicationnameCHEMICAL SCIENCE-
dc.identifier.doi10.1039/d2sc01650h-
dc.contributor.localauthorHong, Sungwoo-
dc.contributor.localauthorBaik, Mu-Hyun-
dc.contributor.nonIdAuthorPudasaini, Bimal-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordPlusEFFECTIVE CORE POTENTIALS-
dc.subject.keywordPlusSOLVATION FREE-ENERGIES-
dc.subject.keywordPlusMOLECULAR CALCULATIONS-
dc.subject.keywordPlusDESIGN-
dc.subject.keywordPlusFUNCTIONALIZATION-
dc.subject.keywordPlusINDOLES-
dc.subject.keywordPlusANALOGS-
dc.subject.keywordPlusAGENTS-
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