Reagent-free intramolecular hydrofunctionalization: a regioselective 6-endo-dig cyclization of o-alkynoylphenols
DC Field | Value | Language |
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dc.contributor.author | Jung, Chanhyun | - |
dc.contributor.author | Li, Siyuan | - |
dc.contributor.author | Lee, Kwanghee | - |
dc.contributor.author | Viji, Mayavan | - |
dc.contributor.author | Lee, Heesoon | - |
dc.contributor.author | Hyun, Soonsil | - |
dc.contributor.author | Lee, Kiho | - |
dc.contributor.author | Kang, Young Kee | - |
dc.contributor.author | Chaudhary, Chhabi Lal | - |
dc.contributor.author | Jung, Jae-Kyung | - |
dc.date.accessioned | 2022-04-01T06:40:43Z | - |
dc.date.available | 2022-04-01T06:40:43Z | - |
dc.date.created | 2022-04-01 | - |
dc.date.issued | 2022-03-21 | - |
dc.identifier.issn | 1463-9262 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/139331 | - |
dc.description.abstract | Solvent-directed intramolecular hydrofunctionalization of readily available o-alkynoylphenols 1 was successfully achieved under reagent-free conditions. The hydrofunctionalization of 1 occurred by nucleophilic attack on the phenolic oxygen followed by consecutive migration of the phenolic H atom to the alkyne center, eventually affording gamma-benzopyranones 2. The phenol O-H group forms intramolecular H-bonds with the carbonyl group, and we predict that these H-bonds can be distorted into their most preferred conformation in the presence of polar solvents. A regioselective 6-endo-dig cyclization seems to be thermodynamically favoured over 5-exo-dig cyclization, as supported by DFT calculations. This strategy is remarkable because it is reagent-free, regioselective, highly atom economical, and highly atom, carbon and reaction mass efficient. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | ROYAL SOC CHEMISTRY | - |
dc.subject | METAL-FREE SYNTHESIS | - |
dc.subject | HYDROGEN-BOND | - |
dc.subject | CATALYST-FREE | - |
dc.subject | HYDROALKOXYLATION | - |
dc.subject | HYDROAMINATION | - |
dc.subject | FLAVONES | - |
dc.subject | ELEMENTS | - |
dc.subject | SOLVENT | - |
dc.title | Reagent-free intramolecular hydrofunctionalization: a regioselective 6-endo-dig cyclization of o-alkynoylphenols | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Lee, Kiho | - |
dc.identifier.doi | 10.1039/d1gc04848a | - |
dc.identifier.scopusid | 2-s2.0-85127329050 | - |
dc.identifier.wosid | 000761978100001 | - |
dc.identifier.bibliographicCitation | GREEN CHEMISTRY, v.24, no.6, pp.2376 - 2384 | - |
dc.relation.isPartOf | GREEN CHEMISTRY | - |
dc.citation.title | GREEN CHEMISTRY | - |
dc.citation.volume | 24 | - |
dc.citation.number | 6 | - |
dc.citation.startPage | 2376 | - |
dc.citation.endPage | 2384 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalResearchArea | Science & Technology - Other Topics | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.relation.journalWebOfScienceCategory | Green & Sustainable Science & Technology | - |
dc.subject.keywordPlus | METAL-FREE SYNTHESIS | - |
dc.subject.keywordPlus | HYDROGEN-BOND | - |
dc.subject.keywordPlus | CATALYST-FREE | - |
dc.subject.keywordPlus | HYDROALKOXYLATION | - |
dc.subject.keywordPlus | HYDROAMINATION | - |
dc.subject.keywordPlus | FLAVONES | - |
dc.subject.keywordPlus | ELEMENTS | - |
dc.subject.keywordPlus | SOLVENT | - |
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