Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates
A direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the meth...
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MDPI AG
2019-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/8/1458 |
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| author | Kimihiro Komeyama Ryusuke Tsunemitsu Takuya Michiyuki Hiroto Yoshida Itaru Osaka |
| author_facet | Kimihiro Komeyama Ryusuke Tsunemitsu Takuya Michiyuki Hiroto Yoshida Itaru Osaka |
| author_sort | Kimihiro Komeyama |
| collection | DOAJ |
| description | A direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the method cannot be applied to the homo-coupling of ubiquitous alkyl tosylates due to the high-lying σ*(C–O) orbital of the tosylates. This paper describes a Ni/Co-catalyzed protocol for the activation of alkyl tosylates on the construction of alkyl dimers under mild conditions. |
| first_indexed | 2024-12-12T03:06:39Z |
| format | Article |
| id | doaj.art-d75addd3aceb450c9a1c7f367334a36f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T03:06:39Z |
| publishDate | 2019-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d75addd3aceb450c9a1c7f367334a36f2022-12-22T00:40:30ZengMDPI AGMolecules1420-30492019-04-01248145810.3390/molecules24081458molecules24081458Ni/Co-Catalyzed Homo-Coupling of Alkyl TosylatesKimihiro Komeyama0Ryusuke Tsunemitsu1Takuya Michiyuki2Hiroto Yoshida3Itaru Osaka4Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima City, Hiroshima 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima City, Hiroshima 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima City, Hiroshima 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima City, Hiroshima 739-8527, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Hiroshima University, 1-4-1 Kagamiyama, Higashi-Hiroshima City, Hiroshima 739-8527, JapanA direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the method cannot be applied to the homo-coupling of ubiquitous alkyl tosylates due to the high-lying σ*(C–O) orbital of the tosylates. This paper describes a Ni/Co-catalyzed protocol for the activation of alkyl tosylates on the construction of alkyl dimers under mild conditions.https://www.mdpi.com/1420-3049/24/8/1458homo-couplingS<sub>N</sub>2-type oxidative additiontransalkylationalkyl tosylatescobalt catalystnickel catalyst |
| spellingShingle | Kimihiro Komeyama Ryusuke Tsunemitsu Takuya Michiyuki Hiroto Yoshida Itaru Osaka Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates Molecules homo-coupling S<sub>N</sub>2-type oxidative addition transalkylation alkyl tosylates cobalt catalyst nickel catalyst |
| title | Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates |
| title_full | Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates |
| title_fullStr | Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates |
| title_full_unstemmed | Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates |
| title_short | Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates |
| title_sort | ni co catalyzed homo coupling of alkyl tosylates |
| topic | homo-coupling S<sub>N</sub>2-type oxidative addition transalkylation alkyl tosylates cobalt catalyst nickel catalyst |
| url | https://www.mdpi.com/1420-3049/24/8/1458 |
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