DC Field | Value | Language |
---|---|---|
dc.contributor.author | Jo, Woohyun | ko |
dc.contributor.author | Baek, Seung-Yeol | ko |
dc.contributor.author | Hwang, Chiwon | ko |
dc.contributor.author | Heo, Joon | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Cho, Seung Hwan | ko |
dc.date.accessioned | 2020-08-31T08:55:24Z | - |
dc.date.available | 2020-08-31T08:55:24Z | - |
dc.date.created | 2020-08-14 | - |
dc.date.created | 2020-08-14 | - |
dc.date.issued | 2020-07 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.30, pp.13235 - 13245 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/276052 | - |
dc.description.abstract | The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biologically active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Experimental and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (alpha-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.title | ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism | - |
dc.type | Article | - |
dc.identifier.wosid | 000557854400039 | - |
dc.identifier.scopusid | 2-s2.0-85089612595 | - |
dc.type.rims | ART | - |
dc.citation.volume | 142 | - |
dc.citation.issue | 30 | - |
dc.citation.beginningpage | 13235 | - |
dc.citation.endingpage | 13245 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/jacs.0c06827 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Jo, Woohyun | - |
dc.contributor.nonIdAuthor | Hwang, Chiwon | - |
dc.contributor.nonIdAuthor | Cho, Seung Hwan | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | FREE REGIOSELECTIVE ALKYLATION | - |
dc.subject.keywordPlus | C-H FUNCTIONALIZATION | - |
dc.subject.keywordPlus | SELECTIVE ALKENYLATION | - |
dc.subject.keywordPlus | DIORGANOZINC COMPOUNDS | - |
dc.subject.keywordPlus | MOLECULAR CALCULATIONS | - |
dc.subject.keywordPlus | NITROGEN-HETEROCYCLES | - |
dc.subject.keywordPlus | FACILE SYNTHESIS | - |
dc.subject.keywordPlus | OXIDES | - |
dc.subject.keywordPlus | ARYLATION | - |
dc.subject.keywordPlus | METHYLATION | - |
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