General Methods for Synthesis of N-Methyliminodiacetic Acid Boronates from Unstable ortho-Phenolboronic Acids
DC Field | Value | Language |
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dc.contributor.author | Ahn, Su-Jin | - |
dc.contributor.author | Lee, Chun-Young | - |
dc.contributor.author | Cheon, Cheol-Hong | - |
dc.date.accessioned | 2021-09-05T08:43:31Z | - |
dc.date.available | 2021-09-05T08:43:31Z | - |
dc.date.created | 2021-06-15 | - |
dc.date.issued | 2014-05-26 | - |
dc.identifier.issn | 1615-4150 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/98492 | - |
dc.description.abstract | A range of N-methyliminodiacetic acid (MIDA) boronates of commercially available but unstable ortho-phenolboronic acid derivatives can be readily prepared through simple condensation between the corresponding phenolboronic acids and MIDA in the presence of molecular sieves. The resulting MIDA boronates are bench-top stable and display a remarkable stability even in DMSO solution at high temperature (>120 degrees C) compared with their parent boronic acids. Moreover, the utility of the resulting MIDA boronate was successfully demonstrated in a cross-coupling reaction using the slow-release protocol to afford the cross-coupled product in much better yield compared with its parent boronic acid counterpart. In addition, an alternative, but more efficient, synthetic route for difficult-to-access ortho-phenol MIDA boronates has been developed through the MIDA boronate formation of methoxymethyl (MOM) protected ortho-phenolboronic acid, followed by deprotection of the MOM group with TMSCl under ambient conditions. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.subject | SMALL-MOLECULE SYNTHESIS | - |
dc.subject | VERSATILE BUILDING-BLOCK | - |
dc.subject | BORONIC ACIDS | - |
dc.subject | NATURAL-PRODUCTS | - |
dc.subject | MIDA BORONATE | - |
dc.subject | DERIVATIVES | - |
dc.subject | STRATEGY | - |
dc.subject | LIGAND | - |
dc.title | General Methods for Synthesis of N-Methyliminodiacetic Acid Boronates from Unstable ortho-Phenolboronic Acids | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Cheon, Cheol-Hong | - |
dc.identifier.doi | 10.1002/adsc.201301023 | - |
dc.identifier.scopusid | 2-s2.0-84901295259 | - |
dc.identifier.wosid | 000337584200014 | - |
dc.identifier.bibliographicCitation | ADVANCED SYNTHESIS & CATALYSIS, v.356, no.8, pp.1767 - 1772 | - |
dc.relation.isPartOf | ADVANCED SYNTHESIS & CATALYSIS | - |
dc.citation.title | ADVANCED SYNTHESIS & CATALYSIS | - |
dc.citation.volume | 356 | - |
dc.citation.number | 8 | - |
dc.citation.startPage | 1767 | - |
dc.citation.endPage | 1772 | - |
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, Applied | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.subject.keywordPlus | SMALL-MOLECULE SYNTHESIS | - |
dc.subject.keywordPlus | VERSATILE BUILDING-BLOCK | - |
dc.subject.keywordPlus | BORONIC ACIDS | - |
dc.subject.keywordPlus | NATURAL-PRODUCTS | - |
dc.subject.keywordPlus | MIDA BORONATE | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | STRATEGY | - |
dc.subject.keywordPlus | LIGAND | - |
dc.subject.keywordAuthor | methoxymethyl (MOM) group | - |
dc.subject.keywordAuthor | N-methyliminodiacetic acid (MIDA) | - |
dc.subject.keywordAuthor | MIDA boronates | - |
dc.subject.keywordAuthor | ortho-phenolboronic acids | - |
dc.subject.keywordAuthor | trimethylsilyl (TMS) chloride | - |
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