From p-Xylene to Ibuprofen in Flow: Three-Step Synthesis by a Unified Sequence of Chemoselective C-H Metalations
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Hyune-Jea | - |
dc.contributor.author | Kim, Heejin | - |
dc.contributor.author | Kim, Dong-Pyo | - |
dc.date.accessioned | 2021-09-01T07:11:15Z | - |
dc.date.available | 2021-09-01T07:11:15Z | - |
dc.date.created | 2021-06-19 | - |
dc.date.issued | 2019-09-06 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/62899 | - |
dc.description.abstract | Ibuprofen was prepared from an inactive and inexpensive p-xylene by three-step flow functionalizations through chemoselective metalations of benzyl positions in sequence using an in situ generated LICKOR-type superbase. The flow approach in the microreactor facilitated the comprehensive exploration of over 100 conditions in the first-step reaction by varying concentrations, temperatures, solvents, and equivalents of reagents, enabling optimal conditions to be found with 95 % yield by significantly suppressing the formation of byproducts, followed by the second C-H metalation step in 95 % yield. Moreover, gram-scale synthesis of ibuprofen in the final step was achieved by biphasic flow reaction of solution-phase intermediate with CO2, isolating 2.3 g for 10 min of operation time. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.subject | FLASH CHEMISTRY | - |
dc.subject | SERIAL MICROREACTIONS | - |
dc.subject | STATIC MIXER | - |
dc.subject | ORGANOLITHIUM | - |
dc.subject | TECHNOLOGY | - |
dc.subject | SUPERBASES | - |
dc.subject | GENERATION | - |
dc.subject | BIODIESEL | - |
dc.subject | EXCHANGE | - |
dc.subject | ARENES | - |
dc.title | From p-Xylene to Ibuprofen in Flow: Three-Step Synthesis by a Unified Sequence of Chemoselective C-H Metalations | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Kim, Heejin | - |
dc.identifier.doi | 10.1002/chem.201903267 | - |
dc.identifier.scopusid | 2-s2.0-85071264884 | - |
dc.identifier.wosid | 000482299000001 | - |
dc.identifier.bibliographicCitation | CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.50, pp.11641 - 11645 | - |
dc.relation.isPartOf | CHEMISTRY-A EUROPEAN JOURNAL | - |
dc.citation.title | CHEMISTRY-A EUROPEAN JOURNAL | - |
dc.citation.volume | 25 | - |
dc.citation.number | 50 | - |
dc.citation.startPage | 11641 | - |
dc.citation.endPage | 11645 | - |
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.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | FLASH CHEMISTRY | - |
dc.subject.keywordPlus | SERIAL MICROREACTIONS | - |
dc.subject.keywordPlus | STATIC MIXER | - |
dc.subject.keywordPlus | ORGANOLITHIUM | - |
dc.subject.keywordPlus | TECHNOLOGY | - |
dc.subject.keywordPlus | SUPERBASES | - |
dc.subject.keywordPlus | GENERATION | - |
dc.subject.keywordPlus | BIODIESEL | - |
dc.subject.keywordPlus | EXCHANGE | - |
dc.subject.keywordPlus | ARENES | - |
dc.subject.keywordAuthor | C-H metalation | - |
dc.subject.keywordAuthor | flow chemistry | - |
dc.subject.keywordAuthor | ibuprofen | - |
dc.subject.keywordAuthor | reaction optimization | - |
dc.subject.keywordAuthor | superbase | - |
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
(02841) 서울특별시 성북구 안암로 14502-3290-1114
COPYRIGHT © 2021 Korea University. All Rights Reserved.
Certain data included herein are derived from the © Web of Science of Clarivate Analytics. All rights reserved.
You may not copy or re-distribute this material in whole or in part without the prior written consent of Clarivate Analytics.