The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones

Simple item page
dc.contributor.authorGeorge, Kwesiga
dc.contributor.authorJulia, Greese
dc.contributor.authorAlexandra, Kelling
dc.contributor.authorEric, Sperlich
dc.contributor.authorBernd, Schmidt
dc.date.accessioned2023-02-01T03:43:14Z
dc.date.available2023-02-01T03:43:14Z
dc.date.issued2022
dc.description.abstractIsoflavones were synthesized via Suzuki−Miyaura coupling of 3-iodochromones and para-methoxybenzene- and para- phenolboronic acid. In our hands, conditions commonly used for similar cross couplings turned out to be unsuccessful or difficult to reproduce, for example, due to the unplanned partial cleavage of MOM-protecting groups. Using Pd(dba)2 as a precatalyst and tricyclohexylphosphine as an activating ligand, reliable cross-coupling conditions were identified. In all cases, notably higher yields of isoflavones were obtained with para-phenolboronic acid than with para-methoxybenzene boronic acid. This observation and the commercial availability of para-phenolboronic acid suggest that for the synthesis of the important 3′-prenyl- or 3′,5′-diprenylisoflavone substitution pattern a synthetic route that introduces the prenyl substituents after the Pd-catalyzed cross-coupling step, thereby avoiding laborious and protecting-group-intensive multistep syntheses of C-prenylated arene boronic acids, is advantageousen_US
dc.description.sponsorshipKabale Universityen_US
dc.identifier.issnhttps://doi.org/10.1021/acs.joc.2c02698
dc.identifier.urihttp://hdl.handle.net/20.500.12493/909
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 United States*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/us/*
dc.subjectThe Suzukien_US
dc.subjectMiyaura Crossen_US
dc.subjectCouplingen_US
dc.subjectClaisen Rearrangementen_US
dc.subjectCrossen_US
dc.subjectMetathesis Approach to Prenylated Isoflavonesen_US
dc.titleThe Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavonesen_US
dc.typeArticleen_US

Files

Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
The Suzuki−Miyaura Cross-Coupling−Claisen.pdf
Size:
3.62 MB
Format:
Adobe Portable Document Format
Description:
https://doi.org/10.1021/acs.joc.2c02698
Download
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.71 KB
Format:
Item-specific license agreed upon to submission
Description:
Download

Collections

Faculty of Science (FSC)