Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst
The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.118 |
| _version_ | 1818913550203092992 |
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| author | Kimihiro Komeyama Shunsuke Sakiyama Kento Iwashita Itaru Osaka Ken Takaki |
| author_facet | Kimihiro Komeyama Shunsuke Sakiyama Kento Iwashita Itaru Osaka Ken Takaki |
| author_sort | Kimihiro Komeyama |
| collection | DOAJ |
| description | The cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved in the oxidative addition and carbometalation steps in the reaction, whereas the chromium salt generates highly nucleophilic allylchromium intermediates from allylcobalt species, without the loss of stereochemical information, to allow the addition to aldehydes. |
| first_indexed | 2024-12-19T23:32:16Z |
| format | Article |
| id | doaj.art-9817a73a8972455ba33e5259f3a30fa2 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T23:32:16Z |
| publishDate | 2018-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-9817a73a8972455ba33e5259f3a30fa22022-12-21T20:01:42ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-06-011411413142010.3762/bjoc.14.1181860-5397-14-118Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalystKimihiro Komeyama0Shunsuke Sakiyama1Kento Iwashita2Itaru Osaka3Ken Takaki4Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Higashi-Hiroshima City 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Higashi-Hiroshima City 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Higashi-Hiroshima City 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Higashi-Hiroshima City 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Higashi-Hiroshima City 739-8527, JapanThe cobalt/chromium-catalyzed three-component coupling of aryl iodides, allenes, and aldehydes has been developed to afford multi-substituted homoallylic alcohols in a diastereoselective manner. Control experiments for understanding the reaction mechanism reveal that the cobalt catalyst is involved in the oxidative addition and carbometalation steps in the reaction, whereas the chromium salt generates highly nucleophilic allylchromium intermediates from allylcobalt species, without the loss of stereochemical information, to allow the addition to aldehydes.https://doi.org/10.3762/bjoc.14.118chromiumcobaltdiastereoselectivehomoallyl alcoholshybrid catalystthree-component coupling |
| spellingShingle | Kimihiro Komeyama Shunsuke Sakiyama Kento Iwashita Itaru Osaka Ken Takaki Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst Beilstein Journal of Organic Chemistry chromium cobalt diastereoselective homoallyl alcohols hybrid catalyst three-component coupling |
| title | Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst |
| title_full | Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst |
| title_fullStr | Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst |
| title_full_unstemmed | Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst |
| title_short | Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst |
| title_sort | three component coupling of aryl iodides allenes and aldehydes catalyzed by a co cr hybrid catalyst |
| topic | chromium cobalt diastereoselective homoallyl alcohols hybrid catalyst three-component coupling |
| url | https://doi.org/10.3762/bjoc.14.118 |
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