The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones
Isoflavones 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...
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| Format: | Article |
| Language: | English |
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American Chemical Society
2023
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| Online Access: | http://hdl.handle.net/20.500.12493/909 |
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| author | George, Kwesiga Julia, Greese Alexandra, Kelling Eric, Sperlich Bernd, Schmidt |
| author_facet | George, Kwesiga Julia, Greese Alexandra, Kelling Eric, Sperlich Bernd, Schmidt |
| author_sort | George, Kwesiga |
| collection | KAB-DR |
| description | Isoflavones 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 advantageous |
| format | Article |
| id | oai:idr.kab.ac.ug:20.500.12493-909 |
| institution | KAB-DR |
| language | English |
| publishDate | 2023 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oai:idr.kab.ac.ug:20.500.12493-9092024-01-17T04:44:52Z The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones George, Kwesiga Julia, Greese Alexandra, Kelling Eric, Sperlich Bernd, Schmidt The Suzuki Miyaura Cross Coupling Claisen Rearrangement Cross Metathesis Approach to Prenylated Isoflavones Isoflavones 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 advantageous Kabale University 2023-02-01T03:43:14Z 2023-02-01T03:43:14Z 2022 Article https://doi.org/10.1021/acs.joc.2c02698 http://hdl.handle.net/20.500.12493/909 en Attribution-NonCommercial-NoDerivs 3.0 United States http://creativecommons.org/licenses/by-nc-nd/3.0/us/ application/pdf American Chemical Society |
| spellingShingle | The Suzuki Miyaura Cross Coupling Claisen Rearrangement Cross Metathesis Approach to Prenylated Isoflavones George, Kwesiga Julia, Greese Alexandra, Kelling Eric, Sperlich Bernd, Schmidt The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones |
| title | The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones |
| title_full | The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones |
| title_fullStr | The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones |
| title_full_unstemmed | The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones |
| title_short | The Suzuki−Miyaura Cross-Coupling−Claisen Rearrangement−Cross-Metathesis Approach to Prenylated Isoflavones |
| title_sort | suzuki miyaura cross coupling claisen rearrangement cross metathesis approach to prenylated isoflavones |
| topic | The Suzuki Miyaura Cross Coupling Claisen Rearrangement Cross Metathesis Approach to Prenylated Isoflavones |
| url | http://hdl.handle.net/20.500.12493/909 |
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